Water → 2,3,4,9-Tetrahydro-6-methoxy-1H-carbazol-1-one

HRID 1679824Notes

Reaction equation

HRID 1679824 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N=C2CCCCC2=O)=[CH:5][CH:4]=1.[OH2:18].S(=O)(=O)(O)O>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][CH:8]=1)[NH:9][C:4]1[C:5](=[O:18])[CH2:6][CH2:7][CH2:8][C:3]2=1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 753926HCID 753926, compound

Product 1

HCID 28568112,3,4,9-Tetrahydro-6-methoxy-1H-carbazol-1-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

232 g. (1 mole) of cyclohexanedione-mono-p-methoxyphenylhydrazone, 1200 ml. of water, 350 g. of sulfuric acid (65 Be) and 100 ml. of ethanol are allowed to boil under reflux for three hours. After cooling down, the mixture is filtered with suction and rendered free from acid by washing with water. The resultant 6-methoxy-1,2,3,4-tetrahydrocarbazol-1-one melts at 222° C. and gives a yield of 193 g. (=90% of the theoretical).

Workup

  1. temperatureunder reflux for three hours
  2. temperatureAfter cooling down
  3. filtrationthe mixture is filtered with suction
  4. washby washing with water

Sources & evidence

ORD record
ord-c8c3d8b5a40a47e1b2c19341d86dfc4c
Source dataset
uspto-grants-1981_06
Patent number
US04271073

Reaction notes

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