Hydrochloric Acid → N-[4-(4-Methoxybenzoyl)phenyl]acetamide

HRID 1716018Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A round-bottomed flask was charged with 4-acetamidobenzoyl chloride (0.95 g, 4.57 mmol), anisole (0.60 mL, 5.48 mmoL) and CH2Cl2 (15 mL). Cooled in an ice bath, AlCl3 (0.93 g, 6.85 mmol) was added in portions. The mixture was stirred at 0° C. for 4 h. The resulting dark brown solution was poured into 1 N HCl (25 mL) with ice and the mixture was extracted with EtOAc (2×60 mL). The combined EtOAc extract was washed with water, brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give brown solid. The crude product was purified by chromatography on a silica gel column eluted with hexanes:EtOAc (1:1) to give 0.55 g (45%) of compound 56 as light brown solid. mp 160-162° C. 1H NMR (400 MHz, CDCl3): δ 2.22 (s, 3H), 3.88 (s, 3H), 6.96 (d, J=8.8 Hz, 2H), 7.34 (br s, 1H), 7.55-7.65 (m, 2H), 7.77 (d, J=8.6 Hz, 2H), 7.79 (d, J=8.8 Hz, 2H). LCMS (ESI): m/z 270 (M+H)+, 268 (M−H)−.

Workup

temperatureCooled in an ice bath
extractionthe mixture was extracted with EtOAc (2×60 mL)
extractionThe combined EtOAc extract
washwas washed with water, brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationthe filtrate was concentrated
customto give brown solid
customThe crude product was purified by chromatography on a silica gel column
washeluted with hexanes:EtOAc (1:1)

Sources & evidence

ORD record: ord-f139281b3992472d92144a19b17388fa
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799828B2

Reaction notes

Loading…