Sodium Nitrate → 5'-Hydroxy-spiro(cyclopentane-1,1'-indan)-3'-one

HRID 426915Notes

Reaction equation

HRID 426915 reaction equation
N[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7]1([CH2:14][CH2:13][CH2:12][CH2:11]1)[CH2:6][C:5]2=[O:15].[N+]([O-])([O-])=[O:17].[Na+]>O>[OH:17][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7]1([CH2:14][CH2:13][CH2:12][CH2:11]1)[CH2:6][C:5]2=[O:15]

Participants

4

Reactant 2

HCID 24268Sodium NitrateHCID 203884255'-Amino-spiro(cyclopentane-1,1'-indan)-3'-one

Product 1

HCID 203884005'-Hydroxy-spiro(cyclopentane-1,1'-indan)-3'-oneYield 98.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5'-amino-spiro(cyclopentane-1,1'-indan)-3'-one (20.1 g; 0.1 mole) 2 N sulphoric acid (150 ml) and ice (30 g) is diazotised at about +5° C. with a solution of sodium nitrate (11 g) in water (25 ml). The solution is filtrated and poured in boiling mixture of 100 ml of water and 10 ml of conc. sulphuric acid. The boiling is continued until the development of nitrogen gas ceases, after which the mixture is chilled and the solid, dark brown substance is filtered off. After drying there are obtained 20 g of a crude product, which is recrystallized from trichloroethylene. Yield 12 g of a light powder of mp. 145° C. 4 g of the substance can be recovered from the mother liquid by means of extraction with 2 N sodium hydroxide and subsequent precipitation with 2 N hydrochloric acid.

Workup

  1. filtrationThe solution is filtrated
  2. additionpoured
  3. additionmixture of 100 ml of water and 10 ml of conc. sulphuric acid
  4. temperatureafter which the mixture is chilled
  5. filtrationthe solid, dark brown substance is filtered off
  6. customAfter drying there

Sources & evidence

ORD record
ord-f4f3e96a7eab416fb23ac8157a7cd070
Source dataset
uspto-grants-1979_10
Patent number
US04172093

Reaction notes

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