HCID 23330143, compound → HCID 23330141, compound

HRID 224730Notes

Reaction equation

HRID 224730 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-8497e3c0556c4255ba74335868ee0c30
Source dataset
uspto-grants-1980_11
Patent number
US04234487

Reaction notes

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