Sodium Hydroxide → HCID 19608044, compound

HRID 1603086Notes

Reaction equation

HRID 1603086 reaction equation
C[O:2][C:3]([C:5]1[CH:22]=[CH:21][C:8]([C:9]([N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13][CH2:12]2)=[O:10])=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>CO>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:9]([N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13][CH2:12]2)=[O:10])=[CH:21][CH:22]=1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 17178209HCID 17178209, compound

Product 1

HCID 19608044HCID 19608044, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(4-methoxycarbonylbenzoyl)-1,2,3,4-tetrahydroquinoline (22.7 g) in methanol (300 ml) is added 5% aqueous sodium hydroxide solution (150 ml) and the mixture is refluxed for 2 hours. Methanol is distilled off under reduced pressure and the resulting residue is acidified with diluted hydrochloric acid, extracted with diethyl ether, and dried over magnesium sulfate. The solvent is distilled off under reduced pressure and the resulting crystal is collected by filtration to give 1-(4-carboxybenzoyl)-1,2,3,4-tetrahydroquinoline (13.2 g) as white powder, m.p. 181-183° C.

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. distillationMethanol is distilled off under reduced pressure
  3. extractionextracted with diethyl ether
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent is distilled off under reduced pressure
  6. filtrationthe resulting crystal is collected by filtration

Sources & evidence

ORD record
ord-9f79cdad07b04824b87d395f081b6556
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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