Sodium Hydroxide → HCID 15288851, compound

HRID 2259302Notes

Reaction equation

HRID 2259302 reaction equation
O[N:2]=[C:3]1[C:7]2[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[C:6]=2[CH2:5][CH2:4]1.[OH-].[Na+]>CCO.O.[Ni]>[CH2:5]1[C:6]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8][C:7]=2[CH:3]([NH2:2])[CH2:4]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 211381HCID 211381, compound

Product 1

HCID 15288851HCID 15288851, compoundYield 90.1%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 3-hydroxyimino-1,2,3,4-tetrahydrocyclopent[b]indole (6 g) in 150 ml of 95% EtOH at 0° C. was added a nickel alloy (Harshaw, Ni-1000P, 10 g) followed by 12.9 grams of sodium hydroxide in 150 ml water. The ice bath was removed after 0.5 hour and the mixture was stirred an additional hour and filtered. The EtOH was removed in vacuo and the product crystallized to provide 5.0 grams of solid. A sample was recrystallized from toluene to provide analytically pure material.

Workup

  1. customThe ice bath was removed after 0.5 hour
  2. filtrationfiltered
  3. customThe EtOH was removed in vacuo
  4. customthe product crystallized

Sources & evidence

ORD record
ord-e62368e203c44a649aa62f070ac3e8d0
Source dataset
uspto-grants-1995_12
Patent number
US05472975

Reaction notes

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