Sodium Hydroxide → HCID 19030984, compound

HRID 483489Notes

Reaction equation

HRID 483489 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14][C:12]2=[O:13])=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>CO>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14][C:12]2=[O:13])=[CH:9][CH:10]=1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19030734HCID 19030734, compound

Product 1

HCID 19030984HCID 19030984, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(4-methoxycarbonylphenyl)-3,4-dihydrocarbostyril (1.84 g) in methanol (40 ml) is added a 5% aqueous sodium hydroxide solution (20 ml) and the mixture is stirred at room temperature overnight. Methanol is distilled off under reduced pressure and to the residue is added water. After the solution is washed with dichloromethane, the aqueous layer is made acidic with concentrated hydrochloric acid and extracted with diethyl ether and dried over magnesium sulfate. The solvent is distilled off under reduced pressure and the resulting residue is purified by silica gel column chromatography, followed by recrystallization from ethanol to give 1-(4-carboxyphenyl)-3,4-dihydrocarbostyril (0.87 g) as pale yellow powders, m.p. 265°-270° C.

Workup

  1. distillationMethanol is distilled off under reduced pressure and to the residue
  2. additionis added water
  3. washAfter the solution is washed with dichloromethane
  4. extractionextracted with diethyl ether
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent is distilled off under reduced pressure
  7. customthe resulting residue is purified by silica gel column chromatography
  8. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-12088da23bef40d9b2a582839deb2970
Source dataset
uspto-grants-1993_07
Patent number
US05225402

Reaction notes

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