Potassium Hydroxide → HCID 20361715, compound

HRID 1679667Notes

Reaction equation

HRID 1679667 reaction equation
C(OC([N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][C:10]3[CH:24]=[CH:23][CH:22]=[CH:21][C:11]=3[C:12]=2[N:16]2[CH:20]=[CH:19][CH:18]=[CH:17]2)[CH2:7]1)=O)C.[OH-].[K+]>C(O)CCC.C1C=CC=CC=1>[N:16]1([C:12]2[C:11]3[CH:21]=[CH:22][CH:23]=[CH:24][C:10]=3[CH:9]=[C:8]3[C:13]=2[CH2:14][CH2:15][NH:6][CH2:7]3)[CH:20]=[CH:19][CH:18]=[CH:17]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 53823225HCID 53823225, compound

Product 1

HCID 20361715HCID 20361715, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 2631-ButanolSolvent

Procedure

A mixture of 2.0 g of 5-(1-pyrrolyl)-1,2,3,4-tetrahydrobenzo[g]isoquinolin-2-yl-carboxylic acid ethyl ester and 4.0 g of potassium hydroxide in 20 ml of n-butanol is boiled for 2 hours. After cooling to room temperature, the mixture is diluted with benzene, washed neutral with water and extracted 3 times with a 10% aqueous tartaric acid solution. The acid solution is washed with ether, made alkaline by the addition of 40% caustic soda solution and extracted with benzene. The benzene extract is washed with water and dried over magnesium sulphate. The title compound is obtained by evaporation of the benzene solvent and converted into the hydrochloride salt having a M.Pt. from 240° (decomposition).

Workup

  1. washwashed neutral with water
  2. extractionextracted 3 times with a 10% aqueous tartaric acid solution
  3. washThe acid solution is washed with ether
  4. additionby the addition of 40% caustic soda solution
  5. extractionextracted with benzene
  6. extractionThe benzene extract
  7. washis washed with water
  8. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-3ffbc54fabd3423d9a5de35538f80d9f
Source dataset
uspto-grants-1978_03
Patent number
US04081543

Reaction notes

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