HCID 59846206, compound → Methyl 4-(3-(4-chloro-2-(phenylamino)phenyl)-3-oxopropyl)benzoate

HRID 1261754Notes

Reaction equation

HRID 1261754 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:13])=[CH:6][CH:5]=1>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:13])=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 59846206HCID 59846206, compound

Product 1

HCID 70817153Methyl 4-(3-(4-chloro-2-(phenylamino)phenyl)-3-oxopropyl)benzoateYield 99.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 500 mL round-bottomed flask equipped with a stirrer was charged with 4-[(E)-3-(4-chloro-2-phenylamino-phenyl)-3-oxo-propenyl]-benzoic acid methyl ester (5.5 g, 14.0 mmol) and ethyl acetate (100 mL). The resulting mixture was stirred under a hydrogen atmosphere for 1 h. At this time, the catalyst was removed by filtration and washed with ethyl acetate. The filtrates were concentrated in vacuo to afford 4-[3-(4-chloro-2-phenylamino-phenyl)-3-oxo-propyl]-benzoic acid methyl ester (5.5 g, 99.5%) as a gummy solid. This material was used without further purification.

Workup

  1. customA 500 mL round-bottomed flask equipped with a stirrer
  2. customAt this time, the catalyst was removed by filtration
  3. washwashed with ethyl acetate
  4. concentrationThe filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-ad707199cc0b44c1aad43dd7c4dc4806
Source dataset
uspto-grants-2013_06
Patent number
US08471027B2

Reaction notes

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