Water → 5-bromo-N-methyl-2-nitroaniline

HRID 1890916Notes

Reaction equation

HRID 1890916 reaction equation
Br[C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][NH2:13].O>C(O)C>[Br:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([NH:13][CH3:12])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 123156462,4-Dibromo-1-nitrobenzene

Product 1

HCID 106095305-bromo-N-methyl-2-nitroanilineYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2,4-dibromo-1-nitro-benzene (2.0 g, 7.14 mmol) in ethanol (50 mL) was added a 40% aqueous solution of methylamine (50 mL). The reaction mixture was stirred at 80° C. in a closed vessel for 3 h, then cooled to 0° C. Water was added and the precipitate was filtered, washed with water, and dried in vacuo to give 1.26 g of (5-bromo-2-nitro-phenyl)-methyl-amine as an orange solid (76% yield): 1H NMR (CDCl3) δ 3.04 (s, 3H), 6.79 (dd, 1H), 7.03 (d, 1H), 8.05 (d, 1H), 8.0-8.1 (broad s, 1H); MS (m/z) 231, 233 [M+H+]+.

Workup

  1. temperaturecooled to 0° C
  2. filtrationthe precipitate was filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-214078624c8849fdb7366d58fea05040
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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