Dimethylformamide → 2-Amino-5-chloro-3-methoxybenzoic acid

HRID 251931Notes

Reaction equation

HRID 251931 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CN(C)C=O.[Cl:18]N1C(=O)CCC1=O>O>[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([Cl:18])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 2557202-Amino-3-methoxybenzoic acid

Product 1

HCID 545958742-Amino-5-chloro-3-methoxybenzoic acidYield 61.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1.67 g of 2-amino-3-methoxybenzoic acid and 100 ml of N,N-dimethylformamide was added 1.3 g of N-chlorosuccinimide at room temperature, and the resulting mixture was stirred at room temperature for 10 hours. Water was poured into the reaction mixture, and a deposited precipitate was collected by filtration to obtain 1.2 g of 2-amino-5-chloro-3-methoxybenzoic acid.

Workup

  1. filtrationa deposited precipitate was collected by filtration

Sources & evidence

ORD record
ord-07d6ef35f3d041359215050c38ce936e
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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