Sodium hydride → 4-[2-Oxo-2-(1,2,3,4-tetrahydro-2-isoquinolinyl)ethoxy]-alpha-oxobenzeneacetic acid ethyl ester

HRID 2225813Notes

Reaction equation

HRID 2225813 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][C:19]([N:21]1[CH2:30][CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22]1)=[O:20]>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][C:19](=[O:20])[N:21]2[CH2:30][CH2:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:22]2)=[CH:8][CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11715332Ethyl 2-(4-hydroxyphenyl)-2-oxoacetateHCID 184672392-Bromo-1-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethan-1-one

Product 1

HCID 537619884-[2-Oxo-2-(1,2,3,4-tetrahydro-2-isoquinolinyl)ethoxy]-alpha-oxobenzeneacetic acid ethyl esterYield 27.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 4-hydroxy-alpha-oxobenzeneacetic acid ethyl ester (0.582 g) in dimethylformamide (8 mL) under argon was treated with 55% sodium hydride (0. 141 g), stirred for 30 minutes and then 2-(2-bromo-1-oxoethyl)-1,2,3,4-tetrahydroisoquinoline (0.762 g) in dimethylformamide (6 mL) was added. The solution was stirred at room temperature for 20 hours and worked up as in Example 20. The crude product was purified by HPLC (ethyl acetate-hexane; 2:3) to yield 0.3 g of 4-[2-oxo-2-(1,2,3,4-tetrahydro-2-isoquinolinyl)ethoxy]-alpha-oxobenzeneacetic acid ethyl ester as an oil.

Workup

  1. stirringThe solution was stirred at room temperature for 20 hours
  2. customThe crude product was purified by HPLC (ethyl acetate-hexane; 2:3)

Sources & evidence

ORD record
ord-c738d49563544107824c9311fa6aceb5
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

Loading…