Sodium hydride → HCID 54247125, compound

HRID 2225826Notes

Reaction equation

HRID 2225826 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)[CH3:2].[H-].[Na+].Br[CH2:18][CH2:19][CH2:20][N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]1=[O:31]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:14])[C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:18][CH2:19][CH2:20][N:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23][C:22]2=[O:31])=[CH:8][CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11715332Ethyl 2-(4-hydroxyphenyl)-2-oxoacetateHCID 19978327HCID 19978327, compound

Product 1

HCID 54247125HCID 54247125, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-hydroxy-alpha-oxobenzeneacetic acid ethyl ester (0.73 g) in dimethylformamide (10 mL) was treated with 55% sodium hydride (0.164 g), stirred for 15 minutes and then 1-(3-bromopropyl)-1,2-dihydro-2-oxoquinoline (1 g) was added and rinsed in with dimethylformamide (4 mL). The mixture was stirred at room temperature for 22 hours and worked up as in Example 20. The residual solid was purified by flash chromatography over silica gel (ethyl acetate-hexane; 1:4). Crystallization of the resulting solid furnished 1.0.g of 4-[3-(1,2-dihydro-2-oxo-1-quinolinyl)propoxy]-alpha-oxobenzeneacetic acid ethyl ester, mp 108°-109° C.

Workup

  1. washrinsed in with dimethylformamide (4 mL)
  2. stirringThe mixture was stirred at room temperature for 22 hours
  3. customThe residual solid was purified by flash chromatography over silica gel (ethyl acetate-hexane; 1:4)
  4. customCrystallization of the resulting solid

Sources & evidence

ORD record
ord-25c44570ffd24f04809c573d54f4f704
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

Loading…