Back to results
US 2011/0319665 A1Published application
Process for Preparing Substituted 2-Nitrobiphenyls
AssigneeBASF SE
InventorsAlexander Korte, Jan Klaas Lohmann, Thomas Grote, Klaus Ebel, Thomas Zierke, Horst Mayer, Ralf Wazulek
Life of this patent
Estimating the term…
Abstract
The present invention relates to a process for preparing substituted 2-nitrobiphenyls and to specific 2-nitrobiphenyls. The invention further relates to a process for preparing 2-aminobiphenyls from such 2-nitrobiphenyls and to a process for preparing (het)arylamides of such 2-aminobiphenyls.
Claims36
1-37. (canceled)
A process for preparing a compound of formula (I)
- wherein
- R1, R2, R3, R4 and R5 are independently of each other selected from hydrogen;
- halogen;
- cyano;
- hydroxyl;
- C1-C6-alkyl, wherein the alkyl group may carry 1, 2 or 3 substituents R6;
- C1-C6-haloalkyl;
- C3-C10-cycloalkyl which may carry 1, 2, 3 or 4 C1-C4-alkyl substituents;
- C3-C10-halocycloalkyl;
- C1-C6-alkoxy;
- C1-C6-haloalkoxy;
- C1-C6-alkylthio;
- C1-C6-haloalkylthio;
- C1-C6-alkylcarbonyl;
- C1-C6-haloalkylcarbonyl;
- C1-C6-alkoxycarbonyl;
- C1-C6-haloalkoxycarbonyl;
- aryl;
- aryl-C1-C4-alkyl;
- arylcarbonyl;
- aryl-C1-C4-alkylcarbonyl;
- aryloxycarbonyl;
- aryl-C1-C4-alkoxycarbonyl, wherein aryl in the six last-mentioned radicals may carry 1, 2, 3 or 4 substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl and a radical R6;
- amino;
- C1-C4-alkylamino;
- di-(C1-C4-alkyl)-amino;
- aminocarbonyl;
- C1-C4-alkylaminocarbonyl;
- and di-(C1-C4-alkyl)-aminocarbonyl;
- or R1 and R2 or R2 and R3 or R3 and R4 or R4 and R5, together with the carbon atoms to which they are bound, form a 5- or 6-membered partially unsaturated or aromatic carbocyclic or heterocyclic ring, where the heterocyclic ring contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of N, O and S as ring members;
- each R6 is independently selected from the group consisting of C3-C10-cycloalkyl which may carry 1, 2, 3 or 4 C1-C4-alkyl substituents;
- C3-C10-halocycloalkyl;
- C1-C4-alkoxy;
- C1-C4-haloalkoxy;
- amino;
- C1-C4-alkylamino;
- di-(C1-C4-alkyl)-amino;
- carboxyl;
- hydroxyl;
- SH and aryl;
- each R7 is independently selected from the group consisting of C1-C4-alkyl, OR8, amino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino and halogen;
- wherein
- R8 is selected from the group consisting of hydrogen, C1-C4-alkyl, a protecting group, and aryl, wherein aryl may carry 1, 2, 3 or 4 substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl and a radical R6;
- and
- a is 0, 1 or 2;
- comprising reacting a compound of formula (II)
- wherein a′ is 0, 1 or 2 and X is a halogen atom,
- with a base
- and, if necessary, aromatizing the resulting product.
46 more elements
A compound of formula (I),
- wherein
- R1, R2, R3, R4 and R5 are independently of each other selected from hydrogen;
- halogen;
- cyano;
- hydroxyl;
- C1-C6-alkyl, wherein the alkyl group may carry 1, 2 or 3 substituents R6;
- C1-C6-haloalkyl;
- C3-C10-cycloalkyl which may carry 1, 2, 3 or 4 C1-C4-alkyl substituents;
- C3-C10-halocycloalkyl;
- C1-C6-alkoxy;
- C1-C6-haloalkoxy;
- C1-C6-alkylthio;
- C1-C6-haloalkylthio;
- C1-C6-alkylcarbonyl;
- C1-C6-haloalkylcarbonyl;
- C1-C6-alkoxycarbonyl;
- C1-C6-haloalkoxycarbonyl;
- aryl;
- aryl-C1-C4-alkyl;
- arylcarbonyl;
- aryl-C1-C4-alkylcarbonyl;
- aryloxycarbonyl;
- aryl-C1-C4-alkoxycarbonyl, wherein aryl in the six last-mentioned radicals may carry 1, 2, 3 or 4 substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl and a radical R6;
- amino;
- C1-C4-alkylamino;
- di-(C1-C4-alkyl)-amino;
- aminocarbonyl;
- C1-C4-alkylaminocarbonyl;
- and di-(C1-C4-alkyl)-aminocarbonyl;
- or R1 and R2 or R2 and R3 or R3 and R4 or R4 and R5, together with the carbon atoms to which they are bound, form a 5- or 6-membered partially unsaturated or aromatic carbocyclic or heterocyclic ring, where the heterocyclic ring contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of N, O and S as ring members;
- each R6 is independently selected from the group consisting of C3-C10-cycloalkyl which may carry 1, 2, 3 or 4 C1-C4-alkyl substituents;
- C3-C10-halocycloalkyl;
- C1-C4-alkoxy;
- C1-C4-haloalkoxy;
- amino;
- C1-C4-alkylamino;
- di-(C1-C4-alkyl)-amino;
- carboxyl;
- hydroxyl;
- SH and aryl;
- each R7 is independently selected from the group consisting of C1-C4-alkyl, OR8, amino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino and halogen;
- wherein
- R8 is selected from the group consisting of hydrogen, C1-C4-alkyl, a protecting group, and aryl, wherein aryl may carry 1, 2, 3 or 4 substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl and a radical R6;
- and
- a is 0, 1 or 2.
42 more elements
A compound of formula (II),
- wherein a′ is 0, 1 or 2 and X is a halogen atom,
- wherein each R7 is independently selected from the group consisting of C1-C4-alkyl, OR8, amino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino and halogen,
- wherein
- R8 is selected from the group consisting of hydrogen, C1-C4-alkyl, a protecting group, and aryl, wherein aryl may carry 1, 2, 3 or 4 substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl and a radical R6;
- and
- each R6 is independently selected from the group consisting of C3-C10-cycloalkyl which may carry 1, 2, 3 or 4 C1-C4-alkyl substituents;
- C3-C10-halocycloalkyl;
- C1-C4-alkoxy;
- C1-C4-haloalkoxy;
- amino;
- C1-C4-alkylamino;
- di-(C1-C4-alkyl)-amino;
- carboxyl;
- hydroxyl;
- SH and aryl.
- a′ is 0, 1 or 2, and
- R1, R2, R4 and R5 are H and R3 is Cl;
- or
- R1 and R5 are H and R2, R3 and R4 are F;
- or
- R1, R2 and R5 are H and R3 and R4 are Cl.
18 more elements
A compound of formula (III),
- R1, R2, R3, R4 and R5 are independently of each other selected from hydrogen;
- halogen;
- cyano;
- hydroxyl;
- C1-C6-alkyl, wherein the alkyl group may carry 1, 2 or 3 substituents R6;
- C1-C6-haloalkyl;
- C3-C10-cycloalkyl which may carry 1, 2, 3 or 4 C1-C4-alkyl substituents;
- C3-C10-halocycloalkyl;
- C1-C6-alkoxy;
- C1-C6-haloalkoxy;
- C1-C6-alkylthio;
- C1-C6-haloalkylthio;
- C1-C6-alkylcarbonyl;
- C1-C6-haloalkylcarbonyl;
- C1-C6-alkoxycarbonyl;
- C1-C6-haloalkoxycarbonyl;
- aryl;
- aryl-C1-C4-alkyl;
- arylcarbonyl;
- aryl-C1-C4-alkylcarbonyl;
- aryloxycarbonyl;
- aryl-C1-C4-alkoxycarbonyl, wherein aryl in the six last-mentioned radicals may carry 1, 2, 3 or 4 substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl and a radical R6;
- amino;
- C1-C4-alkylamino;
- di-(C1-C4-alkyl)-amino;
- aminocarbonyl;
- C1-C4-alkylaminocarbonyl;
- and di-(C1-C4-alkyl)-aminocarbonyl;
- or R1 and R2 or R2 and R3 or R3 and R4 or R4 and R5, together with the carbon atoms to which they are bound, form a 5- or 6-membered partially unsaturated or aromatic carbocyclic or heterocyclic ring, where the heterocyclic ring contains 1, 2, 3 or 4 heteroatoms selected from the group consisting of N, O and S as ring members;
- each R6 is independently selected from the group consisting of C3-C10-cycloalkyl which may carry 1, 2, 3 or 4 C1-C4-alkyl substituents;
- C3-C10-halocycloalkyl;
- C1-C4-alkoxy;
- C1-C4-haloalkoxy;
- amino;
- C1-C4-alkylamino;
- di-(C1-C4-alkyl)-amino;
- carboxyl;
- hydroxyl;
- SH and aryl;
- each R7 is independently selected from the group consisting of C1-C4-alkyl, ORB, amino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino and halogen;
- and
- R8 is selected from the group consisting of hydrogen, C1-C4-alkyl, a protecting group, and aryl, wherein aryl may carry 1, 2, 3 or 4 substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl and a radical R6;
- and
- a′ is 0, 1 or 2.
41 more elements
A compound of formula (III),
- wherein each R7 is independently selected from the group consisting of C1-C4-alkyl, OR8, amino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino and halogen,
- wherein
- R8 is selected from the group consisting of hydrogen, C1-C4-alkyl, a protecting group, and aryl, wherein aryl may carry 1, 2, 3 or 4 substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl and a radical R6;
- each R6 is independently selected from the group consisting of C3-C10-cycloalkyl which may carry 1, 2, 3 or 4 C1-C4-alkyl substituents;
- C3-C10-halocycloalkyl;
- C1-C4-alkoxy;
- C1-C4-haloalkoxy;
- amino;
- C1-C4-alkylamino;
- di-(C1-C4-alkyl)-amino;
- carboxyl;
- hydroxyl;
- SH and aryl;
- a′ is 0, 1 or 2 and
- R1, R2, R4 and R5 are H and R3 is Cl;
- or
- R1 and R5 are H and R2, R3 and R4 are F;
- or
- R1, R2 and R5 are H and R3 and R4 are Cl.
16 more elements
A compound of formula X.1 or X.2
- wherein each R7 is independently selected from the group consisting of C1-C4-alkyl, OR8, amino, C1-C4-alkylamino, di-(C1-C4-alkyl)-amino and halogen,
- wherein
- R8 is selected from the group consisting of hydrogen, C1-C4-alkyl, a protecting group, and aryl, wherein aryl may carry 1, 2, 3 or 4 substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl and a radical R6;
- each R6 is independently selected from the group consisting of C3-C10-cycloalkyl which may carry 1, 2, 3 or 4 C1-C4-alkyl substituents;
- C3-C10-halocycloalkyl;
- C1-C4-alkoxy;
- C1-C4-haloalkoxy;
- amino;
- C1-C4-alkylamino;
- di-(C1-C4-alkyl)-amino;
- carboxyl;
- hydroxyl;
- SH and aryl;
- a′ is 0, 1 or 2, preferably 0, and
- R1, R2, R4 and R5 are H and R3 is Cl;
- or
- R1 and R5 are H and R2, R3 and R4 are F;
- or
- R1, R2 and R5 are H and R3 and R4 are Cl.
16 more elements
Dependencies are inferred from the claim text.