Hydrazine hydrate (1:1) → HCID 57701025, compound

HRID 1186279Notes

Reaction equation

HRID 1186279 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][CH2:13][CH:12]([C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([N+:25]([O-])=O)[CH:23]=3)[NH:18][CH:17]=2)[CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].O.NN>CO.O.[Ni]>[NH2:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[C:16]2[CH:12]1[CH2:13][CH2:14][CH2:15][CH:10]([N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:6])([CH3:7])[CH3:8])[CH2:11]1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57701042HCID 57701042, compound

Product 1

HCID 57701025HCID 57701025, compoundYield 93.4%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of tert-butyl methyl(3-(5-nitro-1H-indol-3-yl)cyclohexyl)carbamate (0.70 g 1.87 mmol) in dry MeOH (15 mL) was added Raney-Ni (0.1 g as a slurry in water) and hydrazine hydrate (1.00 mL, 18.70 mmol). The resulting mixture was immersed in a preheated oil bath and refluxed for 15 min. or until the solution became clear. The reaction was cooled and filtered trough Celite, washed with MeOH (20 mL) and the solvent evaporated. The crude was purified on column chromatography (2 M NH3 in MeOH:CH2Cl2, 2:98) to give the title compound as a light brown solid (0.60 g, 92%). 1H-NMR (CDCl3) δ 1.42 (s, 9H), 1.46-1.72 (m, 6H), 1.88 (ddd, 1H, J=5.4, 12.3, 24.9 Hz), 2.05-2.16 (m, 2H), 2.76 (s, 3H), 3.50 (s, 2H, NH), 4.36-4.51 (m, 1H), 6.64 (dd, 1H, J=2.1, 8.4 Hz), 6.89 (d, 1H, J=2.1 Hz), 7.16 (d, 1H, J=8.4 Hz), 7.28 (s, 1H), 7.76 (s, 1H, NH); EI-MS (m/z, %) 343 (M+, 70), 212 (100).

Workup

  1. customThe resulting mixture was immersed in a preheated oil bath
  2. temperaturerefluxed for 15 min. or until the solution
  3. temperatureThe reaction was cooled
  4. filtrationfiltered trough Celite
  5. washwashed with MeOH (20 mL)
  6. customthe solvent evaporated
  7. customThe crude was purified on column chromatography (2 M NH3 in MeOH:CH2Cl2, 2:98)

Sources & evidence

ORD record
ord-046d459bddae4e519aa66eb80c9054a6
Source dataset
uspto-grants-2014_03
Patent number
US08673909B2

Reaction notes

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