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

HRID 1764692Notes

Reaction equation

HRID 1764692 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 ferrichloride 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-83ae2f87a03242779ead2b5cde1367ce
Source dataset
uspto-grants-1978_09
Patent number
US04117144

Reaction notes

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