Benzylamine → N-Benzyl-3-bromo-2-nitroaniline

HRID 730586Notes

Reaction equation

HRID 730586 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10](F)[C:9]=1[N+:15]([O-:17])=[O:16].[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([NH:25][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([Br:7])[C:9]=1[N+:15]([O-:17])=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 27831521-Bromo-3-fluoro-2-nitrobenzene

Product 1

HCID 57834994N-Benzyl-3-bromo-2-nitroaniline

Procedure

Potassium carbonate (2.58 g, 18.73 mmol) was added to a solution of 1-bromo-3-fluoro-2-nitro-benzene (2.06 g, 9.36 mmol) and benzylamine (1.13 mL, 9.364 mmol) and the resulting suspension was stirred at room temperature for 18 hours. The reaction mixture was poured onto 500 mL of ice water and extracted four times with 100 mL ethyl acetate. The combined organic fractions were dried over sodium sulfate, and concentrated in vacuo to give an oil that was purified by recrystallization from 75 mL refluxing ethanol with 3 mL water. 1.83 g of benzyl-(3-bromo-2-nitro-phenyl)-amine was collected by filtration as fine red needles. MS: 308, 309 (M+H)+.

Workup

  1. extractionextracted four times with 100 mL ethyl acetate
  2. dry with materialThe combined organic fractions were dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give an oil that
  5. customwas purified by recrystallization from 75 mL
  6. temperaturerefluxing ethanol with 3 mL water
  7. filtration1.83 g of benzyl-(3-bromo-2-nitro-phenyl)-amine was collected by filtration as fine red needles

Sources & evidence

ORD record
ord-d33dc636a0274ad1a87ffda5636a9b00
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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