Benzylamine → N-benzyl-2-nitroaniline

HRID 1664299Notes

Reaction equation

HRID 1664299 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C=O)C>[CH2:11]([NH:18][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 521800N-benzyl-2-nitroanilineYield 105.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

According to a modification of a procedure by Goker, H. et. al. (II Farmaco 1998, 53, 415-420) a mixture of 1-fluoro-2-nitro-benzene (1067) (1.1 mL, 10.4 mmol) and benzylamine (2.35 mL, 21.5 mmol) in DMF (5 mL) was heated overnight at 80° C. The reaction mixture was concentrated to give an orange solid which was filtered, washed with water and dried to afford benzyl-(2-nitro-phenyl)-amine (1068) (2.5 g, 100%). 1H NMR 6 (400 MHz, CDCl3) 8.44 (b, 1H, NH), 8.22-8.19 (dd, 1H), 7.41-7.27 (m, 6H), 6.84-6.81 (dd, 1H), 6.70-6.66 (m, 1H), 4.58-4.57 (d, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give an orange solid which
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-200108e5903c48789ae901e29d1fac7f
Source dataset
uspto-grants-2011_10
Patent number
US08039467B2

Reaction notes

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