Sodium Hydroxide → 36077-02-8

HRID 436506Notes

Reaction equation

HRID 436506 reaction equation
C([N:9]1[C:21]2[CH2:20][CH:19]([C:22]([OH:24])=[O:23])[CH2:18][CH2:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[C:13]([Cl:25])[CH:14]=2)(=O)C1C=CC=CC=1.[OH-].[Na+]>>[Cl:25][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:21]1[CH2:20][CH:19]([C:22]([OH:24])=[O:23])[CH2:18][CH2:17][C:16]2=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 21452699HCID 21452699, compound

Product 1

HCID 2145271236077-02-8

Procedure

A stirred mixture of 100 mg. of 9-benzoyl-6-chloro-1,2,3,4-tetrahydrocarbazole-2-carboxylic acid and 5 ml. of 3N sodium hydroxide was heated on a steam bath for 5 minutes and cooled to room temperature. After 1 hour at room temperature, the reaction mixture was further cooled in an ice bath, filtered and the filter cake was washed with 10 drops of cold water. The filter cake was dissolved in 20 ml. of warm water, and the resulting warm solution was made strongly acid with 1N hydrochloric acid. Following filtration, washing with warm water and drying, 56 mg. of (±) 6-chloro-1,2,3,4-tetrahydrocarbazole-2-carboxylic acid was obtained, m.p. 247°-249°.

Workup

  1. additionA stirred mixture of 100 mg
  2. temperaturethe reaction mixture was further cooled in an ice bath
  3. filtrationfiltered
  4. washthe filter cake was washed with 10 drops of cold water
  5. dissolutionThe filter cake was dissolved in 20 ml
  6. temperatureof warm water, and the resulting warm solution
  7. filtrationfiltration
  8. washwashing with warm water
  9. customdrying

Sources & evidence

ORD record
ord-40126086251746908ff1779916af4c97
Source dataset
uspto-grants-1977_02
Patent number
US04009181

Reaction notes

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