Method for producing acetoacetylated aromatic amines
AssigneeLonza Ltd.
InventorsUta Glufke, Paul Hanselmann
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Abstract
A method for producing compounds of general formula (I): wherein R1 and R2, each time they occur and independently of each other, mean hydroxyl, C1-6-alkyl, C1-6-alkoxy, halogen, phenyl or phenoxy; R3 means hydrogen or C1-6-alkyl; m is a whole number from 0 to 4; and n is a whole number from 0 to 5. According to the method, diketene is reacted with an N-phenyl-p-phenylenediamine of general formula (II): wherein R1, R2, R3, m and n have the meanings given above, in the presence of 3 to 40 percent acetic acid and at temperatures of 20 to 100° C. The compounds (I) with R3 is C1-6-alkyl and the enamines can be obtained from these by reaction with ammonia, and their hydration products.
Claims12
A process for the preparation of a compound of the formula:
- in which
- R1 and R2 are at each occurrence independently hydroxyl, C1-6-alkyl, C1-6-alkoxy, halogen, phenyl or phenoxy;
- R2 is hydroxyl, C1-6-alkyl, C1-6-alkoxy, halogen, phenyl or phenoxy;
- R3 is hydrogen or C1-6-alkyl;
- m is an integer from 0 to 4;
- and
- n is an integer from 0 to 5,
- comprising reacting diketene with an N-phenyl-p-phenylenediamine of the formula:
- in which R1, R2, R3, m and n have the meanings indicated above, in the presence of 3 to 40 percent strength acetic acid at a temperature of from 20 to 100° C.
A compound of the formula:
- in which
- R1 and R2 are at each occurrence independently hydroxyl, C1-6-alkyl, C1-6-alkoxy, halogen, phenyl or phenoxy;
- R2 is hydroxyl, C1-6-alkyl, C1-6-alkoxy, halogen, phenyl or phenoxy;
- R3 is C1-6-alkyl;
- m is an integer from 0 to 4;
- and
- n is an integer from 0 to 5.
A process for the preparation of a compound of the formula:
- in which
- R1 and R2 are at each occurrence independently hydroxyl, C1-6-alkyl, C1-6-alkoxy, halogen, phenyl or phenoxy;
- R2 is hydroxyl, C1-6-alkyl, C1-6-alkoxy, halogen, phenyl or phenoxy;
- R3 is C1-6-alkyl;
- m is an integer from 0 to 4;
- and
- n is an integer from 0 to 5,
- comprising reacting a compound of the formula:
- in which R1, R2, R3, m and n have the meanings indicated above, with ammonia.
A compound of the formula:
- in which
- R1 and R2 are at each occurrence independently hydroxyl, C1-6-alkyl, C1-6-alkoxy, halogen, phenyl or phenoxy;
- R2 is hydroxyl, C1-6-alkyl, C1-6-alkoxy, halogen, phenyl or phenoxy;
- R3 is C1-6-alkyl;
- m is an integer from 0 to 4;
- and
- n is an integer from 0 to 5.
A process for the preparation of a compound of the formula:
- in which
- R1 and R2 are at each occurrence independently hydroxyl, C1-6-alkyl, C1-6-alkoxy, halogen, phenyl or phenoxy;
- R2 is hydroxyl, C1-6-alkyl, C1-6-alkoxy, halogen, phenyl or phenoxy;
- R3 is C1-6alkyl;
- m is an integer from 0 to 4;
- and
- n is an integer from 0 to 5,
- comprising catalytically hydrogenating a compound of the formula:
- in which R1, R2, R3, m and n have the meanings indicated above.
Dependencies are inferred from the claim text.