Sodium Hydroxide → HCID 70627092, compound

HRID 1703576Notes

Reaction equation

HRID 1703576 reaction equation
C(OC([N:6]1[CH:14]2[CH:9]([CH:10]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=3)[CH2:11][CH2:12][CH2:13]2)[CH2:8][CH2:7]1)=O)C.[OH-:23].[Na+]>CO>[Cl:22][C:17]1[CH:16]=[C:15]([C:10]2([OH:23])[CH2:11][CH2:12][CH2:13][CH:14]3[CH:9]2[CH2:8][CH2:7][NH:6]3)[CH:20]=[CH:19][C:18]=1[Cl:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70627673HCID 70627673, compound

Product 1

HCID 70627092HCID 70627092, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

24.9 g (3aRS,4SR,7aRS)-4-(3,4-dichlorophenyl)hexahydro-1-indoline carboxylic acid ethyl ester in 240 ml methanol are treated with 240 ml 10N sodium hydroxide and refluxed for 15 hours. The cooled resulting mixture is repeatedly extracted with methylene chloride. The organic phase is extracted with 2N tartaric acid. The acidic phase is made alkaline and extracted with methylene chloride. The methylene chloride phases are dried over magnesium sulphate, and evaporated to give the title compound, in crude free base form, as an oil which is converted, by the addition of an equivalent amount of maleic acid, into the hydrogen maleate. M.Pt. 190°-191°.

Workup

  1. temperaturerefluxed for 15 hours
  2. customThe cooled resulting mixture
  3. extractionis repeatedly extracted with methylene chloride
  4. extractionThe organic phase is extracted with 2N tartaric acid
  5. extractionextracted with methylene chloride
  6. dry with materialThe methylene chloride phases are dried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-b55b2b0271574d668f5b97bf1ca769fa
Source dataset
uspto-grants-1978_11
Patent number
US04124719

Reaction notes

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