Benzylamine → N-benzyl-2-nitroaniline

HRID 1443621Notes

Reaction equation

HRID 1443621 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17]>C1COCC1.C(OCC)(=O)C>[CH2:1]([NH:8][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 521800N-benzyl-2-nitroaniline

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzylamine, (3.1 ml, 28 mmol) was added to 2-fluoronitrobenzene (3 ml, 28.5 mmol) in 20 ml dry THF and the reaction stirred overnight. The crude was diluted with ethyl acetate and washed with said. Bicarbonate and then purified by silica gel chromotography eluting with 10-50% Ethyl acetate in hexanes.

Workup

  1. washwashed
  2. customBicarbonate and then purified by silica gel chromotography
  3. washeluting with 10-50% Ethyl acetate in hexanes

Sources & evidence

ORD record
ord-fc4ccffdd1274764b83bb191eec76775
Source dataset
uspto-grants-2010_02
Patent number
US07662581B1

Reaction notes

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