Hydrazine hydrate (1:1) → 3-(4-(Dimethylamino)cyclohex-1-enyl)-1H-indol-5-amine

HRID 552954노트

반응식

HRID 552954 반응식
[CH3:1][N:2]([CH3:21])[CH:3]1[CH2:8][CH2:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-])=O)[CH:16]=3)[NH:11][CH:10]=2)=[CH:5][CH2:4]1.O.NN>CO.[Ni]>[CH3:1][N:2]([CH3:21])[CH:3]1[CH2:8][CH2:7][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([NH2:18])[CH:16]=3)[NH:11][CH:10]=2)=[CH:5][CH2:4]1

참가 물질

5

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 44430852N,N-dimethyl-4-(5-nitro-1H-indol-3-yl)cyclohex-3-enamine

생성물 1

HCID 574744603-(4-(Dimethylamino)cyclohex-1-enyl)-1H-indol-5-amine수율 98.6%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

실험 절차

A solution of compound 112 (0.21 g, 0.735 mmol) in dry methanol (5 mL) was treated with Ra—Ni (0.05 g) followed by hydrazine hydrate (0.22 mL, 7.359 mmol) at room temperature. The reaction was placed in a pre-heated oil bath and refluxed for 5 min. The reaction brought to room temperature, filtered through celite bed and washed with methanol (2 10 mL). The solvent was evaporated and crude was purified by column chromatography (2 M NH3 in methanol: CH2Cl2, 1:9) to obtain compound 113 (0.185 g, quantitative) as a foam. mp 63-65° C.; 1H NMR (DMSO-d6) δ 1.40-1.52 (m, 1H), 1.97-2.02 (m, 1H), 2.08-2.57 (m, 11H), 4.47 (s, 2H), 5.99 (brs, 1H), 6.47 (dd, 1H, J=1.8, 8.4 Hz), 6.99 (d, 1H, J=0.9 Hz), 7.04 (d, 1H, J=8.7 Hz), 7.13 (d, 1H, J=2.4 Hz), 10.55 (s, 1H); ESI-MS m/z (%): 256 (MH+, 100), 211 (41).

후처리

  1. customThe reaction was placed in a pre-heated oil bath
  2. temperaturerefluxed for 5 min
  3. custombrought to room temperature
  4. filtrationfiltered through celite bed
  5. washwashed with methanol (2 10 mL)
  6. customThe solvent was evaporated
  7. customcrude was purified by column chromatography (2 M NH3 in methanol: CH2Cl2, 1:9)

출처 및 근거

ORD 기록
ord-bd857c492db342afa1e5e72302d8c662
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951940B2

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