Acetic Anhydride → N-(3-bromo-5-nitrophenyl)acetamide

HRID 64084

Reaction equation

HRID 64084 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[Br:8][C:9]1[CH:10]=[C:11]([CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=1)[NH2:12]>>[Br:8][C:9]1[CH:10]=[C:11]([NH:12][C:5](=[O:7])[CH3:6])[CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 44535ar-Bromo-ar-nitrobenzenamine

Product 1

HCID 10658908N-(3-bromo-5-nitrophenyl)acetamideYield 78%

Procedure

Acetic anhydride (14 ml) was added dropwise at 0° C. to 3-bromo-5-nitroaniline (14 g, 64.5 mmol). The mixture was stirred for 30 min at RT and then quenched by the addition of crushed ice. The precipitate formed was filtered and washed with cold water to obtain off-white solid. The solid was dried under vacuum to give the product in 78% yield (13 g). 1H NMR (300 MHz, DMSO-d6): δ 10.54 (br s, 1H), 8.45 (s, 1H), 8.2 (s, 1H), 8.03 (s, 1H), 2.11 (s, 3H).

Workup

  1. customquenched by the addition of crushed ice
  2. customThe precipitate formed
  3. filtrationwas filtered
  4. washwashed with cold water
  5. customto obtain off-white solid
  6. customThe solid was dried under vacuum
  7. customto give the product in 78% yield (13 g)

Sources & evidence

ORD record
ord-e6da30ffaba741e1ab8521151fa9e3e7
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Linked notes

Loading…