p-Aminoacetophenone → HCID 53364581, compound

HRID 918811Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][CH:14]=1>>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][CH:11]=[C:2]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][CH:14]=2)[CH:3]=1

Participants

Reactant 2

HCID 7468p-Aminoacetophenone

HCID 12070Methyl 3-bromobenzoate

Product 1

HCID 53364581HCID 53364581, compound

Procedure

Reaction of methyl 3-bromobenzoate with 4′-aminoacetophenone according to general procedure A provided methyl ester of 6 as a white solid (84% yield). 1H NMR (CDCl3, 500 MHz): δ=7.89 (d, J=8.7 Hz, 2H), 7.85 (s, 1H), 7.73 (m, 1H), 7.36-7.42 (m, 2H), 7.03 (d, J=8.5 Hz, 2H), 6.31 (s, 1H), 3.92 (s, 3H), 2.55 (s, 3H). 13C NMR (CDCl3, 125 MHz): δ=196.7, 167.0, 147.9, 141.3, 131.8, 130.9, 129.9, 129.8, 124.6, 124.2, 121.2, 115.1, 52.5, 26.4.

Sources & evidence

ORD record: ord-897413f548c9494fbae30e4960629d43
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09271961B2

Reaction notes

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