N-cyclopropyl-4,5-difluoro-2-nitroaniline → N1-cyclopropyl-4,5-difluorobenzene-1,2-diamine

HRID 1048953ノート

反応式

HRID 1048953 の反応式
[CH:1]1([NH:4][C:5]2[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:6]=2[N+:13]([O-])=O)[CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([NH:4][C:5]2[C:6]([NH2:13])=[CH:7][C:8]([F:12])=[C:9]([F:11])[CH:10]=2)[CH2:3][CH2:2]1

参加物

4

反応物 1

HCID 86703086N-cyclopropyl-4,5-difluoro-2-nitroaniline

生成物 1

HCID 68053726N1-cyclopropyl-4,5-difluorobenzene-1,2-diamine

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

To the title compound from Step A (1.22 g, 5.69 mmol) were added 10% palladium on carbon (0.122 g, 1.15 mmol) and methanol (28.5 mL). The resulting mixture was stirred under an atmosphere of hydrogen at room temperature overnight. The mixture was then filtered through CELITE® using dichloromethane, and the filtrate was concentrated. Purification by flash chromatography on silica gel (0-30% ethyl acetate in hexanes) provided the title compound: 1H NMR (500 MHz, CDCl3) δ 6.83 (dd, J=12.4, 7.9 Hz, 1 H), 6.51 (dd, J=11.3, 7.8 Hz, 1 H), 3.82 (br s, 1 H), 3.15 (br s, 2 H), 2.40-2.37 (m, 1 H), 0.77-0.73 (m, 2 H), 0.52-0.50 (m, 2 H).

後処理

  1. filtrationThe mixture was then filtered through CELITE®
  2. concentrationthe filtrate was concentrated
  3. customPurification by flash chromatography on silica gel (0-30% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-d9f95678cdfc4c0f9b7b20912fcc376d
出典データセット
uspto-grants-2016_07
特許番号
US09382226B2

反応ノート

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