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US 2016/0102046 A1Published application
Processes for the synthesis of 2-amino-4,6-dimethoxybenzamide and other benzamide compounds
AssigneeAlbemarle Corporation
InventorsAmit THAKKAR, Andrew G. Zeiler, Anthony F. SKUFCA, James J. SPRINGER, Bryce Kelly ASSINK, Mario E. LOZANOV
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Abstract
This invention provides a method for the synthesis of a 2-amino-4,6-dimethoxybenzamide and other benzamides of Compound I: wherein R1, R2, R3, and R4 each independently represent a hydrogen, a C1-C6 alkyl, or a C1-C6 alkoxy; and wherein R6 and R7 each independently represent a hydrogen, a C1-C6 alkyl, a protecting group, or a directing group.
Claims39
A process for producing at least one
- wherein the process comprises:
- (i) combining at least one
- with at least one halogenating agent to produce at least one
- (ii) combining the at least one Compound III with at least one cyanating agent to produce at least one
- and;
- (iii) combining the at least one Compound IV with at least one hydrating agent and/or at least one hydrating catalyst to produce the at least one Compound I,
- wherein R1 and R5 each independently represent a hydrogen, a C1-C6 alkyl, a hydroxy, or a C1-C6 alkoxy;
- wherein R2, R3, and R4 each independently represent a hydrogen, a C1-C6 alkyl, or a C1-C6 alkoxy;
- wherein R6 and R7 each independently represent a hydrogen, a C1-C6 alkyl, a protecting group, or a directing group;
- wherein X represents a halo moiety or a halo-like moiety;
- wherein at least one of R1 and R5 represent a hydrogen;
- and
- provided that in Compound II, R7 represents a protecting group or a directing group, and either
- (1) prior to step (ii), the at least one Compound III is combined with at least one deprotecting agent such that the protecting group or directing group represented by R7 is replaced with a hydrogen or a C1-C6 alkyl, or
- (2) prior to step (iii), the at least one Compound IV is combined with at least one deprotecting agent such that the protecting group or directing group represented by R7 is replaced with a hydrogen or a C1-C6 alkyl.
12 more elements
A process for producing at least one
- wherein the process comprises:
- (i) combining at least one
- with at least one halogenating agent to produce at least one
- (ii) combining the at least one Compound III with at least one cyanating agent to produce at least one
- (iii) combining the at least one Compound IV with at least one first precipitating agent to precipitate the at least Compound IV;
- and
- (iv) combining the at least one Compound IV with at least one hydrating agent and/or at least one hydrating catalyst to produce the at least one Compound I,
- wherein R1 and R5 each independently represent a hydrogen, a C1-C6 alkyl, a hydroxy, or a C1-C6 alkoxy;
- wherein R2, R3, and R4 each independently represent a hydrogen, a C1-C6 alkyl, or a C1-C6 alkoxy;
- wherein R6 and R7 each independently represent a hydrogen, a C1-C6 alkyl, a protecting group, or a directing group;
- wherein X represents a halo moiety or a halo-like moiety;
- wherein at least one of R1 and R5 represent a hydrogen;
- and
- provided that in Compound II, R7 represents a protecting group or a directing group, and either
- (1) prior to step (ii), the at least one Compound III is combined with at least one deprotecting agent such that the protecting group or directing group represented by R7 is replaced with a hydrogen or a C1-C6 alkyl, or
- (2) prior to step (iii), the at least one Compound IV is combined with at least one deprotecting agent such that the protecting group or directing group represented by R7 is replaced with a hydrogen or a C1-C6 alkyl.
13 more elements
A process comprising:
- (i) protecting 3,5-dimethoxyaniline with a protecting agent to produce a protected 3,5-dimethoxyaniline;
- (ii) halogenating the protected 3,5-dimethoxyaniline with a halogenating agent to produce a halogenated protected 3,5-dimethoxyaniline;
- (iii) cyanating the halogenated protected 3,5-dimethoxyaniline with a cyanating agent to produce a cyanated protected 3,5-dimethoxyaniline;
- (iv) deprotecting the cyanated protected 3,5-dimethoxyaniline;
- and
- (v) hydrating the precipitate comprising the cyanated 3,5-dimethoxyaniline to produce 2-amino-4,6-dimethoxybenzamide.
3 more elements
A process comprising:
- (i) protecting 3,5-dimethoxyaniline with a protecting agent to produce a protected 3,5-dimethoxyaniline;
- (ii) halogenating the protected 3,5-dimethoxyaniline with a halogenating agent to produce a halogenated protected 3,5-dimethoxyaniline;
- (iii) cyanating the halogenated protected 3,5-dimethoxyaniline with a cyanating agent to produce a cyanated protected 3,5-dimethoxyaniline;
- (iv) deprotecting the cyanated protected 3,5-dimethoxyaniline and inducing precipitation to produce a precipitate comprising the cyanated 3,5-dimethoxyaniline;
- and
- (v) hydrating the precipitate comprising the cyanated 3,5-dimethoxyaniline to produce 2-amino-4,6-dimethoxybenzamide.
3 more elements
A process comprising:
- (i) protecting 3,5-dimethoxyaniline with a protecting agent to produce a protected 3,5-dimethoxyaniline;
- (ii) halogenating the protected 3,5-dimethoxyaniline with a halogenating agent to produce a halogenated protected 3,5-dimethoxyaniline;
- (iii) cyanating the halogenated protected 3,5-dimethoxyaniline with a cyanating agent to produce a cyanated protected 3,5-dimethoxyaniline;
- (iv) deprotecting the cyanated protected 3,5-dimethoxyaniline and inducing precipitation to produce a first precipitate comprising the cyanated 3,5-dimethoxyaniline;
- (v) re-precipitating the first precipitate comprising the cyanated 3,5-dimethoxyaniline to produce a second precipitate comprising the cyanated 3,5-dimethoxyaniline;
- and
- (vi) hydrating the second precipitate comprising the cyanated 3,5-dimethoxyaniline to produce 2-amino-4,6-di methoxybenzamide.
4 more elements
A process comprising:
- (i) protecting a 3,5-dimethoxyaniline with a protecting agent to produce a protected 3,5-dimethoxyaniline;
- (ii) halogenating the protected 3,5-dimethoxyaniline with a halogenating agent to produce a halogenated protected 3,5-dimethoxyaniline;
- (iii) deprotecting the halogenated protected 3,5-dimethoxyaniline to produce a halogenated 3,5-dimethoxyaniline;
- (iv) precipitating the halogenated 3,5-dimethoxyaniline;
- (v) cyanating the halogenated 3,5-dimethoxyaniline with a cyanating agent to produce a cyanated 3,5-dimethoxyaniline;
- (vi) precipitating the cyanated 3,5-dimethoxyaniline, and
- (vii) hydrating the precipitated cyanated 3,5-dimethoxyaniline to produce 2-amino-4,6-dimethoxybenzamide.
4 more elements
Dependencies are inferred from the claim text.