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

HRID 268234

Reaction equation

HRID 268234 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 vacuum, 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 vacuum, 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-ea5617a276fc42c4a44dcbf7d02b0bae
Source dataset
uspto-grants-1976_03
Patent number
US03947451

Linked notes

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