Butylamine → N-butyl-5-fluoro-2-nitroaniline

HRID 17648

Reaction equation

HRID 17648 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CCN(CC)CC.[CH2:19]([NH2:23])[CH2:20][CH2:21][CH3:22]>CN(C=O)C>[CH2:19]([NH:23][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10])[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 8007ButylamineHCID 8471TriethylamineHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 59566264N-butyl-5-fluoro-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 2,4-difluoronitrobenzene (50 mmol), Et3N (100 mmol) and DMF (80 mL) was added dropwise a solution of n-butylamine (51 mmol) in DMF (20 mL) at rt, and the mixture was stirred at rt for 5 h. The reaction was quenched by cold H2O (100 mL), and the resulting mixture was extracted with EtOAc (4×100 mL). The combined EtOAc extracts were washed with brine (3×60 mL) and dried (anhydrous Na2SO4). The solvent was removed in vacuo to afford the desired 2-n-butylamino-4-fluoronitrobenzene which was used for further transformation.

Workup

  1. customThe reaction was quenched by cold H2O (100 mL)
  2. extractionthe resulting mixture was extracted with EtOAc (4×100 mL)
  3. washThe combined EtOAc extracts were washed with brine (3×60 mL)
  4. dry with materialdried (anhydrous Na2SO4)
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c062db97d9534d338977671ba9c26a1b
Source dataset
uspto-grants-2010_06
Patent number
US07737285B2

Linked notes

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