Hydrochloric Acid → 5'-Chloro-spiro(cyclopentane-1,1'-indan)-3'-one

HRID 426914Notes

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.[Na+].[ClH:21]>O.[Cu]Cl>[Cl:21][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

Conditions

Temperature: 100 °C

Procedure

A mixture of 5'-amino-spiro(cyclopentane-1,1'-indan)-3'-one (20.1 g; 0.1 mole), 23% hydrochloric acid (35 ml), water (76 ml) and ice (3 g) is diazotised at about +5° C. with a solution of sodium nitrate (11 g) in water (25 ml). The clear solution is added to an ice cooled solution of copper(I)chloride(15 g) in 23% hydrochloric acid (150 ml) and water (60 ml). After agitation for 2.5 hours the mixture is heated to 100° C. for a short while and is then allowed to cool. The brown precipitate is sucked off and thoroughly washed with water. Crude yield 20 g (90%). The crude product is purified by distillation in vacuum, bp. 135°-136° C./1,5 mm Hg. A sample is crystallized from n-hexane and then melts at 54° C. The oxime melts at 140° C.

Workup

temperatureto cool
washthoroughly washed with water
distillationThe crude product is purified by distillation in vacuum, bp. 135°-136° C./1,5 mm Hg
customA sample is crystallized from n-hexane

Sources & evidence

ORD record: ord-35e3de191fb844e79999bc99d5eb85ed
Source dataset: uspto-grants-1979_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04172093

Reaction notes

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