2,6-Lutidine → (2E)-N-(2,3-difluorophenyl)-3-phenylacrylamide

HRID 255177Notes

Reaction equation

HRID 255177 reaction equation
[F:1][C:2]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:10](Cl)(=[O:19])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C(C)=CC=CC=1C.BrC1C=C(NC(=O)/C=C/C2C=CC=CC=2)C=CC=1>>[F:1][C:2]1[C:8]([F:9])=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:10](=[O:19])/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 4

HCID 79372,6-LutidineHCID 660233-Phenylprop-2-enoyl chlorideHCID 782782,3-DifluoroanilineHCID 874919(2E)-N-(3-bromophenyl)-3-phenylprop-2-enamide

Product 1

HCID 47450756(2E)-N-(2,3-difluorophenyl)-3-phenylacrylamide

Procedure

The compound was prepared from 2,3-difluoroaniline (5 g, 38.7 mmol) and cinnamoylchloride (6.45 g, 38.7 mmol) in the presence of 2,6-lutidine (6.8 mL, 58 mmol) as described for Intermediate 18 to give a colorless solid, 7.4 g (74%).

Workup

  1. customto give a colorless solid, 7.4 g (74%)

Sources & evidence

ORD record
ord-d4aceeb9203a4e47bde39db791eb8dd6
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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