Acetic Anhydride → Acetamide, N-(4-fluoro-3-nitrophenyl)-

HRID 1435404Notes

Reaction equation

[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12](OC(=O)C)(=[O:14])[CH3:13]>>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:12](=[O:14])[CH3:13])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 677684-Fluoro-3-nitroaniline

Product 1

HCID 67694Acetamide, N-(4-fluoro-3-nitrophenyl)-

Procedure

4-Fluoro-3-nitro-aniline (54.2 g, 0.347 mol) was added in portions to acetic anhydride (200 mL) at room temperature. The reaction mixture was stirred overnight at room temperature. The brown solid was collected and dried in vacuo to give the title compound. Yield: 67.5 g (98%). 1H NMR (400 MHz, CHLOROFORM-D) δ 2.04 (s, 3 H), 7.51 (dd, J=11.23, 9.08 Hz, 1 H), 7.80 (ddd, J=9.08, 4.00, 2.93 Hz, 1 H), 8.47 (dd, J=7.03, 2.73 Hz, 1 H), 10.38 (s, 1 H).

Workup

customThe brown solid was collected
customdried in vacuo

Sources & evidence

ORD record: ord-9166946ebf6e47dfbfc5cbb3f66b5e47
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07615642B2

Reaction notes

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