Methylamine → 2-(4-bromophenyl)-N-methylacetamide

HRID 735553Notes

Reaction equation

BrC1C=CC(CC[C:10]([NH:12]C)=O)=CC=1.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([OH:24])=O)=[CH:17][CH:16]=1.CN>>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([NH:12][CH3:10])=[O:24])=[CH:17][CH:16]=1

Participants

Reactant 3

HCID 6329Methylamine

HCID 74654Benzeneacetic acid, 4-bromo-

HCID 178950553-(4-bromophenyl)-N-methylpropanamide

Product 1

HCID 8425462-(4-bromophenyl)-N-methylacetamideYield 75%

Procedure

Using a procedure analogous to that used to prepare 22A, 2-(4-bromophenyl)acetic acid (1.6 g, 7.0 mmol) was coupled to methylamine to yield 23A (2.0 g, 75%) as a white solid. MS (ESI) m/z 228.20/230.20 (M+H)+.

Sources & evidence

ORD record: ord-41e1d6476d514bb2b58d2b75876faa14
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592331B2

Reaction notes

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