4-Nitroaniline → Benzenamine, 2-bromo-4-nitro-

HRID 1363417Notes

Reaction equation

HRID 1363417 reaction equation
[Br:1]N1C(=O)CCC1=O.[N+:9]([C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1)([O-:11])=[O:10]>CN(C=O)C>[Br:1][C:17]1[CH:18]=[C:12]([N+:9]([O-:11])=[O:10])[CH:13]=[CH:14][C:15]=1[NH2:16]

Participants

4

Reactant 2

HCID 74754-NitroanilineHCID 67184N-bromobutanimide

Product 1

HCID 25840Benzenamine, 2-bromo-4-nitro-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
27.5 °C

Procedure

N-Bromosuccinimide (26 g, 146 mmol) was added to a stirred solution of 4-nitro aniline (20 g, 145 mmol) in dry DMF (75 mL) in portions under stirring at temperature 25-30° C. Reaction mixture was stirred for 30 min. It was poured over crushed ice slowly under vigorous stirring, filtered and dried, to afford the title compound.

Workup

  1. customReaction mixture
  2. stirringwas stirred for 30 min
  3. additionIt was poured
  4. customover crushed ice slowly under vigorous stirring
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-da0ee00bb004428280ce544ba9e5599d
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

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