Sodium hydride → HCID 15053135, compound

HRID 2225754Notes

Reaction equation

HRID 2225754 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.Cl.Cl[CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1.[H-].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester

Product 1

HCID 15053135HCID 15053135, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.50 g) and 2-chloromethylquinoline hydrochloride (0.60 g) were suspended in 6 mL of dimethylformamide and 60% sodium hydride (0.224 g) was added. When gas evolution ceased, the bath temperature was raised to 50° C. for 2 hours. The reaction mixture was quenched with 0.1 mL of acetic acid and was diluted with ethyl acetate (75 mL). The mixture was washed with water (2×25 mL) and brine (1×25 mL), dried (MgSO4) and chromatographed over 100 g of silica gel, eluting with dichoromethane-ethyl acetate (50: 1) to give 0.39 g of 4-[(2-quinolinyl)methoxy]-alpha-oxobenzeneacetic acid methyl ester, mp 109°-110° C.

Workup

  1. customThe reaction mixture was quenched with 0.1 mL of acetic acid
  2. additionwas diluted with ethyl acetate (75 mL)
  3. washThe mixture was washed with water (2×25 mL) and brine (1×25 mL)
  4. dry with materialdried (MgSO4)
  5. customchromatographed over 100 g of silica gel
  6. washeluting with dichoromethane-ethyl acetate (50: 1)

Sources & evidence

ORD record
ord-012b2d29a1614da098fb914507ed4720
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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