Acetic Acid → 5'-Chlorospiro(cyclopentane-1,3'-indoline)-2-one

HRID 1112775Notes

Reaction equation

HRID 1112775 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2(CC[CH2:11][CH2:10]2)[C:2]1=O.[ClH:15].[C:16]([OH:19])(=O)[CH3:17]>>[Cl:15][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH2:2][C:3]12[CH2:10][CH2:11][CH2:17][C:16]1=[O:19]

Participants

4

Reactant 3

HCID 176Acetic Acid2×HCID 313Hydrochloric AcidHCID 3633431',2'-Dihydrospiro[cyclopentane-1,3'-indole]-2'-one

Product 1

HCID 227631105'-Chlorospiro(cyclopentane-1,3'-indoline)-2-one

Procedure

Spiro(cyclopentane-1,3'-indoline)-2'-one (18.7 g; 0.10 moles) is dissolved in acetic acid (50 ml) containing 100 mg of ferricloride hexahydrate, cooled in ice-water and drop-wise treated under agitation with a solution of clorine in acetic acid (82 ml of a solution containing 7.8 g per 100 ml). After the addition air is blown through the solution to eliminate a possible excess of clorine as well as hydrogen cloride. The crystallized product (8.7 g) is sucked off and the filtrate is concentrated in vaccum, upon which an additional product quantity (7.3 g) is obtained. After recrystallization from ethanol the substance melts at 201°-202° C.

Workup

  1. concentrationthe filtrate is concentrated in vaccum, upon which an additional product quantity (7.3 g)
  2. customis obtained
  3. customAfter recrystallization from ethanol the substance melts at 201°-202° C.

Sources & evidence

ORD record
ord-39c7f0d798d94dd8b99c3c03bd8dd29c
Source dataset
uspto-grants-1978_10
Patent number
US04123543

Reaction notes

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