5'-Nitro-spiro(cyclopentane-1,1'-indan)-3'-one → 5'-Amino-spiro(cyclopentane-1,1'-indan)-3'-one

HRID 426913Notes

Reaction equation

HRID 426913 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9]1([CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:8][C:7]2=[O:17])([O-])=O>CO.[Ni].Cl>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9]1([CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:8][C:7]2=[O:17]

Participants

5

Reactant 1

HCID 203884395'-Nitro-spiro(cyclopentane-1,1'-indan)-3'-one

Product 1

HCID 203884255'-Amino-spiro(cyclopentane-1,1'-indan)-3'-oneYield 97%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 5'-nitro-spiro(cyclopentane-1,1'-indan)-3'-one (23.1 g; 0.1 mole) in methanol (250 ml) is hydrogenated in a shaking autoclave at about 4 atg with a Raney-nickel catalyst at 40°-60° C. The mixture is chilled, the catalyst filtered off and washed with methanol, after which the filtrate is evaporated to dryness. A light yellow powder is obtained (19.5 g; yield 97%). Said powder is dissolved in 2 N hydrochloric acid and extracted with ether, and then the aqueous phase is neutralized with 2 N sodium hydroxid solution. The precipitate is filtered off, washed with water and dried, and 18.8 g of a yellow-white crystal powder is obtained. A sample is recrystallized twice from benzene and then melts at 125° C.

Workup

  1. temperatureThe mixture is chilled
  2. filtrationthe catalyst filtered off
  3. washwashed with methanol
  4. customafter which the filtrate is evaporated to dryness
  5. customA light yellow powder is obtained (19.5 g; yield 97%)
  6. extractionextracted with ether
  7. filtrationThe precipitate is filtered off
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-f22244648c924964a41744d842c1e82e
Source dataset
uspto-grants-1979_10
Patent number
US04172093

Reaction notes

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