Sodium Hydroxide → HCID 19004461, compound

HRID 2225755Notes

Reaction equation

HRID 2225755 reaction equation
C[O:2][C:3](=[O:24])[C:4](=[O:23])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[CH:7][CH:6]=1.[OH-].[Na+]>CO.O1CCCC1>[N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][C:13]=1[CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:4](=[O:23])[C:3]([OH:24])=[O:2])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15053135HCID 15053135, compound

Product 1

HCID 19004461HCID 19004461, compoundYield 43.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[(2-quinolinyl)methoxy]-alpha-oxobenzeneacetic acid methyl ester (0.34 g) in methanol (2 mL) and tetrahydrofuran (8 mL) was treated with 1N sodium hydroxide (1.1 mL) and a white precipitate formed. After 5 minutes, the reaction mixture was concentrated and the residue was acidified with excess hydrochloric acid. The residue was triturated with water (25 mL) and dichloromethane-tetrahydrofuran (150 mL, 9:1) and the solids were crystallized twice from dimethylsulfoxide-acetonitrile-water to give 0.142 g of 4-[(2-quinolinyl)methoxy]-alpha-oxo-benzeneacetic acid, mp 225°-228° C.

Workup

  1. customa white precipitate formed
  2. concentrationthe reaction mixture was concentrated
  3. customThe residue was triturated with water (25 mL) and dichloromethane-tetrahydrofuran (150 mL, 9:1)
  4. customthe solids were crystallized twice from dimethylsulfoxide-acetonitrile-water

Sources & evidence

ORD record
ord-cc2492f2220345c48e03dab0e18c9ea4
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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