HCID 23330143, compound → HCID 23330141, compound

HRID 1447982Notes

Reaction equation

HRID 1447982 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][C:8]3(OCC[O:15]3)[CH2:7][CH2:6][C:5]2=1>C(O)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][C:8](=[O:15])[CH2:7][CH2:6][C:5]2=1

Participants

3

Reactant 1

HCID 23330143HCID 23330143, compound

Product 1

HCID 23330141HCID 23330141, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

A suspension of 6-chloro-2,2-ethylenedioxy-1,2,3,4-tetrahydrocarbazole in 200 ml. of 1:1 acetic acid/water was heated at reflux under nitrogen for 1.5 hours. The mixture was filtered hot and the filtrate was cooled in an ice bath and again filtered. Crystallization of the solid from methylene chloride/30°-60° petroleum ether gave 5.74 g. (26% yield) of 6-chloro-1,2,3,4-tetrahydrocarbazole-2-one as a flocculent solid, mp 194°-196°.

Workup

  1. temperatureat reflux under nitrogen for 1.5 hours
  2. filtrationThe mixture was filtered hot
  3. temperaturethe filtrate was cooled in an ice bath
  4. filtrationagain filtered
  5. customCrystallization of the solid from methylene chloride/30°-60° petroleum ether
  6. customgave 5.74 g

Sources & evidence

ORD record
ord-98e1b481059c40aba3e5aaf00f392c07
Source dataset
uspto-grants-1979_12
Patent number
US04179443

Reaction notes

Loading…