Dimethylformamide → HCID 86632549, compound

HRID 251958Notes

Reaction equation

HRID 251958 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[C:9]([Cl:12])[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]([CH3:11])=[C:9]([Cl:12])[C:8]([Cl:18])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 8274632-Amino-4-chloro-3-methylbenzoic acid

Product 1

HCID 86632549HCID 86632549, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 0.34 g of 2-amino-4-chloro-3-methylbenzoic acid and 10 ml of N,N-dimethylformamide was added 0.26 g of N-chlorosuccinimide at room temperature, and the mixture was stirred at room temperature for 5 hours. After 30 ml of water was poured into the reaction mixture, the mixture was extracted with ethyl acetate three times. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 0.22 g of 2-amino-4,5-dichloro-3-methylbenzoic acid of the formula:

Workup

  1. extractionthe mixture was extracted with ethyl acetate three times
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5d05e7e993794497bddd87bd320598da
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

Loading…