Benzyl Bromide → N-Benzyl-N,2-dimethyl-5-nitro-aniline

HRID 2061439Notes

Reaction equation

HRID 2061439 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][NH:8][C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[CH3:18].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([N:8]([CH3:7])[C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[CH3:18])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 13317617N,2-dimethyl-5-nitroaniline

Product 1

HCID 66915963N-Benzyl-N,2-dimethyl-5-nitro-aniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

K2CO3 (270 mg) is added to a solution of N,2-dimethyl-5-nitro-aniline (214.5 mg, 1.29 mmol) and benzyl bromide (0.2 mL, 1.7 mmol) in DMF (4 mL). The mixture is heated for 12 h to 70° C. under stirring. Volatiles are evaporated at reduced pressure. Chromatography of the residue (silica gel, hexane/EtOAc 4:1) yields N-Benzyl-N,2-dimethyl-5-nitro-aniline.

Workup

  1. temperatureThe mixture is heated for 12 h to 70° C.
  2. customVolatiles are evaporated at reduced pressure

Sources & evidence

ORD record
ord-b51fcc4a141d4ed3be319acd473b2337
Source dataset
uspto-grants-2012_10
Patent number
US08283356B2

Reaction notes

Loading…