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

HRID 1603613Notes

Reaction equation

HRID 1603613 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=1)[NH2:5].[C:12](OC(=O)C)(=[O:14])[CH3:13]>N1C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:12](=[O:14])[CH3:13])[CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=1

Participants

5

Reactant 2

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

Product 1

HCID 10658908N-(3-bromo-5-nitrophenyl)acetamideYield 91.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

28.40 g (0.131 mol) of 3-bromo-5-nitroaniline were dissolved in 250 ml of pyridine and treated with 30 ml (0.317 mol) of acetic anhydride. The mixture was stirred at room temperature for 18 hrs. and subsequently at 40° C. for 2 hrs. Then, the residue was digested in water and the precipitate was filtered off. The filter material was rinsed with a large amount of water and dried at 45° C. in a high vacuum. There were obtained 31.0 g (91.5%) of N-(3-bromo-5-nitrophenyl)-acetamide as orange-yellow crystals. MS (ISP): me/e=260, 258 (C8H8BrN2O3+).

Workup

  1. waitand subsequently at 40° C. for 2 hrs
  2. filtrationthe precipitate was filtered off
  3. washThe filter material was rinsed with a large amount of water
  4. customdried at 45° C. in a high vacuum

Sources & evidence

ORD record
ord-849c30a95b584c4cb3098744679e5144
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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