Potassium Hydroxide → HCID 70509915, compound

HRID 326095Notes

Reaction equation

HRID 326095 reaction equation
Cl.C([O:4][C:5](=[O:29])[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[N:9]2[C:18]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)=[N:19][CH2:20][CH2:21][C:8]=12)C.[OH-].[K+]>O.CO>[ClH:28].[CH3:17][O:16][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]1[C:18]([C:22]3[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=3)=[N:19][CH2:20][CH2:21][C:8]1=[C:7]2[CH2:6][C:5]([OH:29])=[O:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 70509442HCID 70509442, compound

Product 1

HCID 70509915HCID 70509915, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

117.2 g (0.27 mol) of 7-methoxy-1-(p-chlorophenyl)-3,4-dihydro-pyrimido[1,6-a]indole-5-acetic acid ethyl ester hydrochloride are introduced, while stirring, into a solution of 550 g of potassium hydroxide in 200 ml of water and 1500 ml of methanol. The mixture is stirred for 10 hours at room temperature, the methanol is distilled off in vacuo, the residue is dissolved in 1500 ml of ice-water, and 700 ml of concentrated hydrochloric acid are added to the solution while cooling with ice. The separated hydrochloride is filtered with suction and recrystallised from 2300 ml of 50% ethanol to yield 7-methoxy-1-(p-chlorophenyl)-3,4-dihydro-pyrimido[1,6-a]indole-5-acetic acid hydrochloride in the form of yellowish crystals having a melting point of 225°-228° (with decomposition).

Workup

  1. distillationthe methanol is distilled off in vacuo
  2. dissolutionthe residue is dissolved in 1500 ml of ice-water
  3. addition700 ml of concentrated hydrochloric acid are added to the solution
  4. temperaturewhile cooling with ice
  5. filtrationThe separated hydrochloride is filtered with suction
  6. customrecrystallised from 2300 ml of 50% ethanol

Sources & evidence

ORD record
ord-02e6674bc0104507b439d62ae7a55cc9
Source dataset
uspto-grants-1984_04
Patent number
US04444768

Reaction notes

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