Acetanilide → HCID 762824, compound

HRID 1028370Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](Br)=[C:6]([N+:11]([O-])=O)[CH:5]=1.[C:15]1([NH:21][C:22](=O)[CH3:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:22]([CH3:23])=[N:11][C:6]=2[CH:5]=1)=[O:14]

Participants

Reactant 2

HCID 904Acetanilide

HCID 2736829Methyl 4-bromo-3-nitrobenzoate

Product 1

HCID 762824HCID 762824, compoundYield 59%

Procedure

The title compound was prepared with the analogous procedure described in example 1 using 4-Bromo-3-nitrobenzoic acid methyl ester (130 mg, 0.5 mmol) and N-phenylacetamide (81 mg, 0.6 mmol) as starting materials to yield the title compound as colorless crystals (78 mg, 59%). mp 108-110° C. 1H NMR (DMSO) δ 2.55 (s, 3 H), 3.78 (s, 3 H), 7.30 (d, J=8.2 Hz, 1 H), 7.52-7.71 (m, 5 H), 7.92 (d, J=8.2 Hz, 1 H), 8.30 (br s, 1 H); 13C NMR δ 13.6, 52.1, 110.8, 118.5, 124.7, 124.8, 127.0, 129.7, 130.1, 134.0, 137.9, 153.7, 157.8, 166.2. HRMS (FAB): cal. for C16H15N2O2 [M+H]+: 267.1134; found: 267.1128.

Workup

customThe title compound was prepared with the analogous procedure

Sources & evidence

ORD record: ord-d829d4f3195e486e9c9152323153f020
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735586B2

Reaction notes

Loading…