Hydrochloric Acid → 3-(Dimethylamino)-6-ethoxycarbonyl-1,2,3,4-tetrahydrocarbazole

HRID 461550Notes

Reaction equation

HRID 461550 reaction equation
[CH3:1][N:2]([CH3:10])[CH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[C:11]([C:14]1[CH:19]=[CH:18][C:17]([NH:20]N)=[CH:16][CH:15]=1)([OH:13])=[O:12].Cl.[CH2:23](O)[CH3:24]>>[CH3:1][N:2]([CH3:10])[CH:3]1[CH2:8][C:7]2[C:18]3[C:17](=[CH:16][CH:15]=[C:14]([C:11]([O:13][CH2:23][CH3:24])=[O:12])[CH:19]=3)[NH:20][C:6]=2[CH2:5][CH2:4]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 120894-Hydrazinobenzoic acidHCID 103745454-(Dimethylamino)cyclohexan-1-one

Product 1

HCID 128917863-(Dimethylamino)-6-ethoxycarbonyl-1,2,3,4-tetrahydrocarbazole

Procedure

A solution of 15.5 g. of 4-dimethylaminocyclohexanone and 15.2 g. of 4-carboxyphenylhydrazine in 200 ml. of 5-N hydrogen chloride in ethyl alcohol was refluxed for twentyfour hours and the reaction mixture was evaporated to dryness under reduced pressure. The residue was dissolved in water, the aqueous solution was made alkaline with dilute sodium hydroxide and extracted with methylene dichloride and the extract was evaporated to dryness under reduced pressure to give, after recrystallization from isopropyl alcohol, 17.8 g. of 3-(dimethylamino)-6-ethoxycarbonyl-1,2,3,4-tetrahydrocarbazole, m.p. 188°-190° C.

Workup

  1. customthe reaction mixture was evaporated to dryness under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with methylene dichloride
  4. customthe extract was evaporated to dryness under reduced pressure
  5. customto give
  6. customafter recrystallization from isopropyl alcohol, 17.8 g

Sources & evidence

ORD record
ord-75519fa448e048689b8fa07d8653aef6
Source dataset
uspto-grants-1977_12
Patent number
US04062864

Reaction notes

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