Hydrochloric Acid → HCID 23470202, compound

HRID 1077371Notes

Reaction equation

HRID 1077371 reaction equation
[C:1]([NH:4][CH:5]1[CH2:17][C:16]2[C:15]3[C:10](=[C:11]([F:18])[CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[CH2:7][CH2:6]1)(=O)[CH3:2].C(NC1CCC(=O)CC1)(=O)C.Cl.FC1C=CC=CC=1NN.Cl>C(O)C>[CH2:1]([NH:4][CH:5]1[CH2:17][C:16]2[C:15]3[C:10](=[C:11]([F:18])[CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[CH2:7][CH2:6]1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 538565N-(4-Oxocyclohexyl)acetamideHCID 2723910Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1)HCID 12891806HCID 12891806, compound

Product 1

HCID 23470202HCID 23470202, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3-Acetamido-8-fluoro-1,2,3,4-tetrahydrocarbazole -- A solution of 7.8 g. of 4-acetamidocyclohexanone and 8.1 g. of 2-fluorophenylhydrazine hydrochloride in 75 ml. of absolute ethyl alcohol and 25 ml. of 5-N hydrogen chloride in absolute ethyl alcohol was heated under reflux for two hours, cooled, filtered, and the filtrate was evaporated to dryness. The residue was dissolved in chloroform and adsorbed on a column of aluminum oxide. Dilution with ether yielded first a small amount of side-product followed by the desired product which was recrystallized by dissolving in methyl alcohol, adding toluene, and evaporation of the methyl alcohol, to give 10.5 g. of 3-acetamido-8-fluoro-1,2,3,4-tetrahydrocarbazole, m.p. 202°-204°C.

Workup

  1. temperatureunder reflux for two hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customthe filtrate was evaporated to dryness
  5. dissolutionThe residue was dissolved in chloroform
  6. customDilution with ether yielded first a small amount of side-product

Sources & evidence

ORD record
ord-9f8de6af3bb148a9a0747397848eb536
Source dataset
uspto-grants-1976_05
Patent number
US03959309

Reaction notes

Loading…