Hydrazine hydrate (1:1) → HCID 76568135, compound

HRID 1728191Notes

Reaction equation

HRID 1728191 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:30])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=4[N+:23]([O-])=O)[CH2:14][C:13](=[O:26])[NH:12][CH:11]3[C:27]([CH3:29])=[CH2:28])[C:5]2=[CH:4][CH:3]=1.NN.O>CO.[Ni]>[NH2:23][C:17]1[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:16]=1[CH:15]1[CH2:14][C:13](=[O:26])[NH:12][CH:11]([C:27]([CH3:29])=[CH2:28])[C:10]21[C:5]1[C:6](=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[NH:8][C:9]2=[O:30]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 76567907HCID 76567907, compound

Product 1

HCID 76568135HCID 76568135, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

The reaction mixture of racemic (2′R,3R,4′S)-6-chloro-4′-(5-chloro-2-nitro-phenyl)-2′-isopropenylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (290 mg, 0.65 mmol), Raney Ni (39 mg) and NH2NH2.H2O (320 mg) in methanol was stirred at 80° C. for 0.5 h. The mixture was cooled to 4° C., and concentrated. To the residue were added ethyl acetate (10 mL) and water (10 mL). The organic layer was separated, washed with brine, dried over MgSO4 and concentrated. The residue was purified by column chromatography to give the title compound as a solid (Yield: 260 mg).

Workup

  1. temperatureThe mixture was cooled to 4° C.
  2. concentrationconcentrated
  3. additionTo the residue were added ethyl acetate (10 mL) and water (10 mL)
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-6e422cb4566f4f5f9a8b60d7325f69d6
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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