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

HRID 2043520노트

반응식

HRID 2043520 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-b78110b66c3d4338810f6a1dadf0b165
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586620B2

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