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

HRID 243121Notes

Reaction equation

HRID 243121 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].CC[N:14](C(C)C)[CH:15]([CH3:17])[CH3:16].C(N)(C)C>C(#N)C>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([NH:14][CH:15]([CH3:17])[CH3:16])[CH:7]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 679672,4-DifluoronitrobenzeneHCID 81531Diisopropylethylamine

Product 1

HCID 106318075-Fluoro-N-isopropyl-2-nitroanilineYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,4-Difluoro-1-nitrobenzene (2.00 g, 12.57 mmol) was dissolved in acetonitrile (20 mL) and DIPEA (2.2 mL, 12.57 mmol) added, followed by isopropylamine (1.07 mL, 12.57 mmol). The bright yellow mixture was stirred at RT overnight. The resultant mixture was concentrated in vacuo and the residue purified by column chromatography (silica gel, gradient 0-5% EtOAc in cyclohexane) to afford the title compound as a yellow gum (2.1 g, 99%). Contaminated with some unreacted 2,4-difluoro-1-nitrobenzene, but used in the next step without any further purification. 1H NMR (CDCl3, 400 MHz): δ 8.20 (1H, dd, J=9.53, 6.21 Hz), 6.48 (1H, dd, J=11.71, 2.63 Hz), 6.33 (1H, m), 3.80-3.64 (1H, m), 1.33 (6H, d, J=6.36 Hz)

Workup

  1. concentrationThe resultant mixture was concentrated in vacuo
  2. customthe residue purified by column chromatography (silica gel, gradient 0-5% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-6f72fbf8b8554a299f2dc59a372b8a85
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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