Ammonia → 3-Carbamoyl-5-nitrobenzoic acid

HRID 1192992Notes

Reaction equation

HRID 1192992 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([O-:16])=O)[CH:7]=[C:8]([C:10]([O:12]C)=[O:11])[CH:9]=1)([O-:3])=[O:2].[OH-].[NH4+:18].N>O>[NH2:18][C:14]([C:6]1[CH:7]=[C:8]([CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:10]([OH:12])=[O:11])=[O:16]

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 14923Ammonium HydroxideHCID 6931682Monomethyl-5-nitroisophthalate

Product 1

HCID 227493663-Carbamoyl-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The ammonium salt of 3-(aminocarbonyl)-5-nitrobenzoic acid (Compound I or C-I) is prepared from 5-nitro-1,3-benzenedicarboxylic acid, 1-methyl ester (“MME”) with ammonium hydroxide. The reaction is preferably carried out in an aqueous solvent, e.g., ammonia in water, and at elevated temperatures. Preferably, the reaction mixture contains a molar excess of ammonia relative to MME. In one embodiment, the product, C-I, is obtained as a solid, centrifuged or filtered, washed with cold aqueous ammonia then by cold water and finally dried.

Workup

  1. customIn one embodiment, the product, C-I, is obtained as a solid
  2. filtrationcentrifuged or filtered
  3. washwashed with cold aqueous ammonia
  4. dry with materialby cold water and finally dried

Sources & evidence

ORD record
ord-de315d28c7414207a08cd2078be6d9a5
Source dataset
uspto-grants-2014_03
Patent number
US08680334B2

Reaction notes

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