m-Aminoacetanilide → (3-Acetylamino-phenylamino)-phenyl-acetic acid ethyl ester

HRID 76987

Reaction equation

HRID 76987 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.Br[CH:13]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15].CCN(C(C)C)C(C)C>C(#N)C>[CH2:17]([O:16][C:14](=[O:15])[CH:13]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:18]

Participants

5

Reactant 3

HCID 7604m-AminoacetanilideHCID 81531DiisopropylethylamineHCID 97780Ethyl bromophenylacetate

Product 1

HCID 59401202(3-Acetylamino-phenylamino)-phenyl-acetic acid ethyl esterYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

N-(3-Aminophenyl)acetamide (371 mg, 2.47 mmol), ethyl 2-bromo-2-phenylacetate (0.29 mL, 1.64 mmol), and DIPEA (0.43 mL, 2.47 mmol) are dissolved in acetonitrile (5 mL). The reaction is heated under MW irradiation at 100° C. for 30 minutes. Conversion complete by UPLC/MS-UV. Acetonitrile is evaporated and the crude residue is purified by flash chromatography (DCM/EtOAc=8/2) to obtain intermediate I92 as a colorless oil (440 mg, 86% yield).

Workup

  1. customAcetonitrile is evaporated
  2. customthe crude residue is purified by flash chromatography (DCM/EtOAc=8/2)

Sources & evidence

ORD record
ord-710f35955fd94a4ca0538bffada3a3b1
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Linked notes

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