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

HRID 1048953노트

반응식

HRID 1048953 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d9f95678cdfc4c0f9b7b20912fcc376d
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382226B2

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