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5-Chloro-2-methoxybenzoyl chloride → 4-[2-(5-Chloro-2-methoxybenzamido)-ethyl]-phenylacetic acid

HRID 1706478
Notes
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Reaction equation

HRID 1706478 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1.[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([O:26][CH3:27])=[C:21]([CH:25]=1)[C:22](Cl)=[O:23]>>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([O:26][CH3:27])=[C:21]([CH:25]=1)[C:22]([NH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][CH:5]=1)=[O:23].[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([O:26][CH3:27])=[C:21]([CH:25]=1)[C:22]([NH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:8][CH:9]=1)=[O:23]
ParticipantsProcedureSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 123841765-Chloro-2-methoxybenzoyl chlorideHCID 20463409Ethyl 4-(2-aminoethyl)benzeneacetate

Product 2

HCID 234530454-[2-(5-Chloro-2-methoxybenzamido)-ethyl]-phenylacetic acidHCID 23453116HCID 23453116, compound

Procedure

In an analogous manner, by the reaction of ethyl 4-(2-aminoethyl)-phenylacetate with 5-chloro-2-methoxybenzoyl chloride, there is obtained, via ethyl 4-[2-(5-chloro-2-methoxybenzamido)-ethyl]-phenylacetate (oil), 4-[2-(5-chloro-2-methoxybenzamido)-ethyl]-phenylacetic acid; m.p. 127°-128° C., after recrystallization from 75% acetic acid.

Sources & evidence

ORD record
ord-2b91fb32e5e343bc8a1c3f085ae65764
Source dataset
uspto-grants-1980_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04207341

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes