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

HRID 1077352

Reaction equation

HRID 1077352 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 24 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-f58102c95cb64599bbe9428bcf8b7997
Source dataset
uspto-grants-1976_05
Patent number
US03959309

Linked notes

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