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

HRID 243121노트

반응식

HRID 243121 반응식
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

참가 물질

5

반응물 3

HCID 6363IsopropylamineHCID 679672,4-DifluoronitrobenzeneHCID 81531Diisopropylethylamine

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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)

후처리

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

출처 및 근거

ORD 기록
ord-6f72fbf8b8554a299f2dc59a372b8a85
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653089B2

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