Water → N-(2-(benzyloxy)-4-bromo-6-nitrophenyl)acetamide

HRID 1258451Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:15]=[C:14]([Br:16])[CH:13]=[C:12]([N+:17]([O-:19])=[O:18])[C:10]=1[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](OC(=O)C)(=[O:22])[CH3:21].O>C(O)(=O)C.S(=O)(=O)(O)O>[CH2:1]([O:8][C:9]1[CH:15]=[C:14]([Br:16])[CH:13]=[C:12]([N+:17]([O-:19])=[O:18])[C:10]=1[NH:11][C:20](=[O:22])[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2-(benzyloxy)-4-bromo-6-nitroaniline (33.0 g, 102 mmol, WO 2004054984) and acetic anhydride (14.5 mL, 153 mmol) in acetic acid (90 mL) was added concentrated sulfuric acid (2 drops) at 70° C. The mixture was stirred at 70° C. for 20 minutes. After cooling to room temperature, water (800 mL) was added, and the formed precipitate was collected by filtration and washed with diisopropyl ether to afford the title compound as a brown solid (30.9 g, 83%).

Workup

temperatureAfter cooling to room temperature
filtrationthe formed precipitate was collected by filtration
washwashed with diisopropyl ether

Sources & evidence

ORD record: ord-c0ecf06f14404eaaa862e3274a8840b0
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466166B2

Reaction notes

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