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US 2004/0132982 A1Published application
Process for the preparation of aromatic azo-compounds
AssigneeGenerics [UK] Limited
InventorsVinayak G. Gore, Manoj M. Ghadge, Vishakha R. Shembekar, R. Venkat Raman
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Abstract
The present invention relates to a process for the preparation of aromatic azo-compounds, in particular 3,3′-azo-bis(6-hydroxybenzoic acid) (olsalazine) and its salts and derivatives.
Claims18
A process for the preparation of an aromatic azo-compound 4
- 7
- or a salt thereof, comprising the step of treating aromatic amino-compounds 5 and 6
- 8
- with (i) hydrogen peroxide and acetic acid, followed by (ii) conc. sulphuric acid, to yield aromatic azo-compound 4 or a salt thereof, wherein
- each m and each n is independently 0, 1, 2, 3, 4 or 5, and
- each R1 and each R2 is independently an optionally substituted alkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, alkylaryl, alkenylaryl or alkynylaryl group which may include one or more heteroatoms N, O or S in its carbon skeleton, —F, —Cl, —Br, —I, —CF3, —CCl3, —CBr3, —CI3, —OH, —SH, —NH2, —CN, —NO2, —COOH, —R3—O—R4, —R3—S—R4, —R3—SO—R4, —R3—SO2—R4, —R3—SO2—OR4—R3O—SO2—R4, —R3—SO2—N(R4)2, —R3—NR4—SO2—R4, —R3O—SO2—OR4, —R3O—SO2—N(R4)2, —R3—NR4—SO2—OR4, —R3—NR4—SO2—N(R4)2, —R3—N(R4)2, —R3—N(R4)3+, —R3—P(R4)2, —R3—Si(R4)3, —R3—CO—R4, —R3—CO—OR4, —R3O—CO—R4, —R3—CO—N(R4)2, —R3—NR4—CO—R4, —R3O—CO—OR4, —R3O—CO—N(R4)2, —R3—NR4—CO—OR4, —R3—NR4—CO—N(R4)2, —R3—CS—R4, —R3—CS—OR4, —R3O—CS—R4, —R3—CS—N(R4)2, —R3—NR4—CS—R4, —R3O—CS—OR4, —R3O—CS—N(R4)2, —R3—NR4—CS—OR4 or —R3—NR4—CS—N(R4)2, all optionally protected, wherein
- each —R3— is independently a chemical bond, a C1-C10 alkylene, C1-C10 alkenylene or C1-C10 alkynylene group, and
- each —R4 is independently hydrogen, unsubstituted C1-C6 alkyl or unsubstituted C6-C10 aryl.
5 more elements
A process for the preparation of 3,3′-azo-bis(6-hydroxybenzoic acid) 1
- 9
- or a salt or derivative thereof, comprising the step of treating a 5-amino salicyclic acid derivative 2a
- 10
- or a salt or derivative thereof, with (i) hydrogen peroxide and acetic acid, followed by (ii) conc. sulphuric acid, to yield a 3,3′-azo-bis(6-hydroxybenzoic acid derivative) 1a
- 11
- or a salt or derivative thereof, wherein
- X is OR, SR or N(R)2,
- when X is OR or SR, R is independently an optionally substituted alkyl alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, alkylaryl, alkenylaryl or alkynylaryl group which may include one or more heteroatoms N, O or S in its carbon skeleton, hydrogen, —Si(alkyl)3 or —Sn(alkyl)3, and
- when X is N(R)2, each R is independently an optionally substituted alkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, alkylaryl, alkenylaryl or alkynylaryl group which may include one or more heteroatoms N, O or S in its carbon skeleton, hydrogen, —SO2-(aryl), —NH2, —NH(alkyl) or —NH(aryl), or both R together form an optionally substituted cycloheteroalkyl, cycloheteroalkenyl or heteroaryl group.
6 more elements
Dependencies are inferred from the claim text.