5-Chloro-2-methoxybenzoyl chloride → 4-(5-Chloro-2-methoxybenzamidomethyl)-phenylacetic acid

HRID 1706470Notes

Reaction equation

HRID 1706470 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].Cl.[NH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:18][CH:17]=1>CC(C)=O.[OH-].[Na+].O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([NH:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=[O:24])=[CH:18][CH:17]=1)=[O:8]

Participants

6

Reactant 2

HCID 123841765-Chloro-2-methoxybenzoyl chlorideHCID 53407881(4-(Aminomethyl)phenyl)acetic acid--hydrogen chloride (1/1)

Product 1

HCID 234531114-(5-Chloro-2-methoxybenzamidomethyl)-phenylacetic acidYield 22.1%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 5.0 g 5-chloro-2-methoxybenzoyl chloride in 10 ml acetone is added, with ice cooling, to a solution of 5.0 g 4-aminomethyl-phenylacetic acid hydrochloride in 25 ml 2 N aqueous sodium hydroxide solution and 25 ml acetone. The reaction mixture is then stirred for 3 hours at ambient temperature, diluted with water, filtered with charcoal and the filtrate acidified with 2 N hydrochloric acid. The precipitate obtained is filtered off with suction and dried and then recrystallized from ethyl acetate/petroleum ether. There is obtained 1.8 g (21% of theory) 4-(5-chloro-2-methoxybenzamidomethyl)-phenylacetic acid; m.p. 140°-141° C.

Workup

  1. filtrationfiltered with charcoal
  2. customThe precipitate obtained
  3. filtrationis filtered off with suction
  4. customdried
  5. customrecrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-b5cfec0d2a58425186eafcbf670fd436
Source dataset
uspto-grants-1980_06
Patent number
US04207341

Reaction notes

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