Hydrochloric Acid → 3-(Dimethylamino)-8-ethoxycarbonyl-1,2,3,4-tetrahydrocarbazole

HRID 1077353Notes

Reaction equation

HRID 1077353 reaction equation
CN(C)C1CC2C3C(=C(C(O)=O)C=CC=3)NC=2CC1.Cl.Cl.[CH3:22][N:23]([CH3:42])[CH:24]1[CH2:36][C:35]2[C:34]3[C:29](=[C:30]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:31]=[CH:32][CH:33]=3)[NH:28][C:27]=2[CH2:26][CH2:25]1>C(O)C>[CH3:22][N:23]([CH3:42])[CH:24]1[CH2:36][C:35]2[C:34]3[C:29](=[C:30]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:31]=[CH:32][CH:33]=3)[NH:28][C:27]=2[CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 128918623-(Dimethylamino)-8-carboxy-1,2,3,4-tetrahydrocarbazoleHCID 234702783-(Dimethylamino)-8-ethoxycarbonyl-1,2,3,4-tetrahydrocarbazole hydrochloride

Product 1

HCID 128917873-(Dimethylamino)-8-ethoxycarbonyl-1,2,3,4-tetrahydrocarbazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4.5 g. of 3-(dimethylamino)-8-carboxy-1,2,3,4-tetrahydrocarbazole (Example 39) in 150 ml. of 5-N hydrogen chloride in ethyl alcohol was heated under reflux for thirty hours. The solution was evaporated to dryness under reduced pressure and the residue was recrystallized from ethanol to give 3 g. of 3-(dimethylamino)-8-ethoxycarbonyl-1,2,3,4-tetrahydrocarbazole hydrochloride, m.p. 263°-264°C.

Workup

  1. temperatureunder reflux for thirty hours
  2. customThe solution was evaporated to dryness under reduced pressure
  3. customthe residue was recrystallized from ethanol
  4. customto give 3 g

Sources & evidence

ORD record
ord-bc4933749f104025a3fb85685e23a41f
Source dataset
uspto-grants-1976_05
Patent number
US03959309

Reaction notes

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