Isopropylamine → 5-Fluoro-N-isopropyl-2-nitroaniline

HRID 502902Notes

Reaction equation

HRID 502902 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].C([O-])([O-])=O.[K+].[K+].[CH:18]([NH2:21])([CH3:20])[CH3:19]>C1COCC1>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([NH:21][CH:18]([CH3:20])[CH3:19])[CH:7]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 11430Potassium CarbonateHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 106318075-Fluoro-N-isopropyl-2-nitroanilineYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 2,4-difluoro-1-nitrobenzene (4.77 g, 30 mmol) and K2CO3 (4.14 g, 30 mmol) in THF (30 mL) was added isopropyl amine (1.77 g, 30 mmol) in THF (10 mL) at 0° C. After being stirred for 13 h, the insoluble materials were removed by pad of Celite and the filtrate was consentrated under reduced pressure to give title compound (5.25 g, 88%) as a pale yellow oil.

Workup

  1. customthe insoluble materials were removed by pad of Celite

Sources & evidence

ORD record
ord-9ad1406e140146bdb4ebf724a625cadc
Source dataset
uspto-grants-2010_08
Patent number
US07776885B2

Reaction notes

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