Sodium Hydroxide → HCID 21452703, compound

HRID 436508Notes

Reaction equation

HRID 436508 reaction equation
C([O:3][C:4]([CH:6]1[CH2:18][CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:19])[CH:14]=3)[N:9]([CH3:20])[C:8]=2[CH2:7]1)=[O:5])C.[OH-].[Na+]>C(O)C>[Cl:19][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:20])[C:8]1[CH2:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:18][CH2:17][C:16]2=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54298054HCID 54298054, compound

Product 1

HCID 21452703HCID 21452703, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.6 g. of 6-chloro-9-methyl-1,2,3,4-tetrahydrocarbazole-2-carboxylic acid ethyl ester, 25 ml. of ethanol and 25 ml. of 3N sodium hydroxide was refluxed and stirred for 6 hours. Upon cooling to room temperature, the reaction mixture was concentrated to dryness under reduced pressure. The residue was dissolved in water (300 ml.) and filtered. The filter cake was washed with water (4 × 50 ml.) and dried, yielding 4.2 g. of product, m.p. 259°-260° . Upon recrystallization from ethyl acetate, 4.0. g. of 6-chloro-9-methyl-1,2,3,4-tetrahydrocarbazole-2-carboxylic acid was obtained, m.p. 259°-260°.

Workup

  1. additionA mixture of 4.6 g
  2. concentrationthe reaction mixture was concentrated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in water (300 ml.)
  4. filtrationfiltered
  5. washThe filter cake was washed with water (4 × 50 ml.)
  6. customdried
  7. customyielding 4.2 g
  8. customUpon recrystallization from ethyl acetate, 4.0

Sources & evidence

ORD record
ord-81b118e714a24d0983762ea617353f79
Source dataset
uspto-grants-1977_02
Patent number
US04009181

Reaction notes

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