Glycine → 2-[(Carboxymethyl)amino]-4-chlorobenzoic acid

HRID 1532423Notes

Reaction equation

HRID 1532423 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH-].[K+].Cl[C:10]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].[NH2:20][CH2:21][C:22]([OH:24])=[O:23]>O.[Cu]>[C:22]([CH2:21][NH:20][C:10]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13])([OH:24])=[O:23]

Participants

7

Reactant 4

HCID 750GlycineHCID 57872,4-Dichlorobenzoic AcidHCID 11430Potassium CarbonateHCID 14797Potassium Hydroxide

Product 1

HCID 111071412-[(Carboxymethyl)amino]-4-chlorobenzoic acidYield 71.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

To a solution of potassium carbonate (10.3 g), potassium hydroxide (10.3 g), 2,4-dichlorobenzoic acid (VI) (15 g) and glycine (VII) (10.31 g) in water (150 ml) was added copper powder (0.38 g) and the resulting mixture was refluxed for 2 hours. Hereinafter, the resulting reaction solution was treated in the same manner as in Example 1 to give 12.8 g of the desired compound (yield, 71.2%).

Workup

  1. temperaturethe resulting mixture was refluxed for 2 hours
  2. customHereinafter, the resulting reaction solution
  3. additionwas treated in the same manner as in Example 1

Sources & evidence

ORD record
ord-0a3bc2f7886b4418ba763ae0e954547e
Source dataset
uspto-grants-2001_03
Patent number
US06201121B1

Reaction notes

Loading…