Sodium Hydroxide → 1-Methyl-1,2,3,4-tetrahydrocarbazole-1-propionic Acid

HRID 65625Notes

Reaction equation

HRID 65625 reaction equation
[CH3:1][C:2]12[CH2:17][CH2:16][C:15](=[O:18])[N:13]3[C:14]1=[C:6]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=13)[CH2:5][CH2:4][CH2:3]2.[OH-:19].[Na+]>C(O)C>[CH3:1][C:2]1([CH2:17][CH2:16][C:15]([OH:19])=[O:18])[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 122918901,2,3,3a,4,5-hexahydro-3a-methyl-6H-pyrido[3,2,1-jk]carbazol-6-one

Product 1

HCID 122918941-Methyl-1,2,3,4-tetrahydrocarbazole-1-propionic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1,2,3,3a,4,5-hexahydro-3a-methyl-6H-pyrido[3,2,1-jk]carbazol-6-one (0.5 g), described in Example 40, in ethanol (10 ml) and 10% sodium hydroxide solution (10 ml) is heated at reflux for 3 hr. The mixture is concentrated, diluted with water and washed with ether. The aqueous phase is rendered acidic with conc. HCl and extracted with chloroform. Concentration of the chloroform extract yields the title compound as a solid, mp 204°-206° C., identical to the product of Example 69.

Workup

  1. temperatureat reflux for 3 hr
  2. concentrationThe mixture is concentrated
  3. additiondiluted with water
  4. washwashed with ether
  5. extractionextracted with chloroform
  6. extractionConcentration of the chloroform extract

Sources & evidence

ORD record
ord-adbc9dad967b4687a75d1ee9230c8c45
Source dataset
uspto-grants-1978_12
Patent number
US04128560

Reaction notes

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