2-Nitroaniline → N-benzyl-2-nitroaniline

HRID 1485395Notes

Reaction equation

HRID 1485395 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH2:10])([O-:3])=[O:2].[H-].[Na+].Br[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH2:14]([NH:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 69462-NitroanilineHCID 7498Benzyl BromideHCID 24758Sodium hydride

Product 1

HCID 521800N-benzyl-2-nitroanilineYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-nitrobenzenamine (5.0 g, 36.2 mmol) was dissolved in 100 mL of THF under N2 atmosphere, 60% NaH (1.7 g, 43.4 mmol) was added at 0° C., and the mixture was stirred for 30 min at room temperature. (Bromomethyl)benzene (7.4 g, 43.4 mmol) was added at 0° C. and the reaction was stirred at 80° C. overnight. The solvent was evaporated in vacuo and the residue was purified by combi-flash (PE:EA=2:1) to give N-benzyl-2-nitroaniline as a yellow solid (2.92 g, 36%). 1H NMR (300 MHz, CD3OD): δ 4.65 (d, J=6 Hz, 2H), 6.69 (t, J=7.2 Hz, 1H), 6.94 (d, J=9 Hz, 1H), 7.25-7.50 (m, 5H), 8.09 (d, J=8.4 Hz, 1H), 8.62-8.68 (m, 1H).

Workup

  1. stirringthe reaction was stirred at 80° C. overnight
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was purified by combi-flash (PE:EA=2:1)

Sources & evidence

ORD record
ord-375d0b2bcce74c4db2fc5b2cca9f2647
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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