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

HRID 1532422Notes

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>[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

Conditions

Temperature: 30 °C

Procedure

To a solution of potassium carbonate (50.7 g), potassium hydroxide (47.3 g), 2,4-dichlorobenzoic acid (VI) (70 g) and glycine (VII) (96.3 g) in water (700 ml) was added cupric chloride (0.7 g) and the resulting solution was refluxed for 4 hours. After this reaction solution was cooled to 30° C., the copper salt was removed by filtration and concentrated hydrochloric acid (288 g) was added to the resultant filtrate at temperature of not more than 40° C. Then, the resulting precipitate was collected by filtration, washed with water and dried under vacuum to give 73.8 g of 2-carboxymethylamino-4-chlorobenzoic acid (yield, 87.7%).

Workup

temperaturethe resulting solution was refluxed for 4 hours
customthe copper salt was removed by filtration and concentrated hydrochloric acid (288 g)
additionwas added to the resultant filtrate at temperature of not more than 40° C
filtrationThen, the resulting precipitate was collected by filtration
washwashed with water
customdried under vacuum

Sources & evidence

ORD record: ord-1ee1fd9c940240df90eadf9e87d87369
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06201121B1

Reaction notes

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