Hydrazine hydrate (1:1) → HCID 57701032, compound

HRID 1186282Notes

Reaction equation

HRID 1186282 reaction equation
[CH2:1]([N:3]([CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([N+:26]([O-])=O)[CH:24]=3)[NH:19][CH:18]=2)[CH2:12]1)[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH3:2].O.NN>CO.O.[Ni]>[NH2:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[C:17]2[CH:13]1[CH2:14][CH2:15][CH2:16][CH:11]([N:3]([CH2:1][CH3:2])[C:4](=[O:10])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[CH2:12]1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 57701041HCID 57701041, compound

Product 1

HCID 57701032HCID 57701032, compoundYield 98.9%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of tert-butyl ethyl(3-(5-nitro-1H-indol-3-yl)cyclohexyl)carbamate (0.70, g 1.81 mmol) in dry MeOH (15 mL) was added Raney-Ni (0.1 g as a slurry in water) and hydrazine hydrate (0.90 mL, 18.10 mmol). The resulting mixture was immersed in a preheated oil bath and refluxed for 15 minutes 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 brownish solid (0.64 g, quantitative). 1H-NMR (CDCl3) δ 1.12 (t, 3H, J=6.8 Hz), 1.45 (s, 9H), 1.53-1.69 (m, 3H), 1.71-1.79 (m 1H), 1.82-1.92 (m, 1H), 2.07-2.17 (m, 2H), 3.06-3.24 (m, 2H), 3.43-3.56 (m, 1H), 4.43 (s, 1H), 6.64 (dd, 1H, J=2.1, 8.4 Hz), 6.89 (d, 1H, J=2.1 Hz), 7.15 (d, 1H, J=8.4 Hz), 7.26 (s, 1H), 7.33 (s, 1H), 7.82 (s, 1H); EI-MS (m/z, %) 357 (M+, 70), 212 (100).

Workup

  1. customThe resulting mixture was immersed in a preheated oil bath
  2. temperaturerefluxed for 15 minutes 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-76d514dd88414ecd8509e7ef0fa646ba
Source dataset
uspto-grants-2014_03
Patent number
US08673909B2

Reaction notes

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