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

HRID 243121ノート

反応式

HRID 243121 の反応式
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

参加物

5

反応物 3

HCID 6363IsopropylamineHCID 679672,4-DifluoronitrobenzeneHCID 81531Diisopropylethylamine

生成物 1

HCID 106318075-Fluoro-N-isopropyl-2-nitroaniline収率 99%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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)

後処理

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

出典と根拠

ORDレコード
ord-6f72fbf8b8554a299f2dc59a372b8a85
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

反応ノート

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