N-(2-acetyl-4-nitro-phenyl)-acetamide → 1-(2-amino-5-nitrophenyl)ethanone

HRID 1251293Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4 (85.56 g, 0.39 moles) and 6 N HCl (600 mL) was stirred for 2 h at 80° C. The suspension was filtered, washed with water, and air-dried to afford 1-(2-amino-5-nitro-phenyl)ethanone 5 (54.95 g, 79% yield). 1HNMR(400 MHz, DMSO-d6) δ2.61 (s, 3H), 6.86 (d, 1H, J=9.4 Hz), 8.07 (dd, 1H, J=2.6, 9.4 Hz), 8.61 (d, 1H, J=2.6), 8.08-8.61 (bs, 2H); MS m/z 180 (M+).

Workup

filtrationThe suspension was filtered
washwashed with water
customair-dried

Sources & evidence

ORD record: ord-c99d490816144092b9d4c267d708e3ac
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06342079B1

Reaction notes

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