Diethyl Ether → HCID 20375614, compound

HRID 1448821Notes

Reaction equation

HRID 1448821 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:22]=[CH:21][C:7]([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH3:19])=[CH:11][C:10]2=[O:20])=[CH:6][CH:5]=1.[C:23](OCC)(=[O:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25].CCOCC>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH2:19][C:23](=[O:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:11][C:10]2=[O:20])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 12114996N-350S

Product 1

HCID 20375614HCID 20375614, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (18 g.; 60% w/w dispersion in oil, washed as described in Example 1) was stirred in dry dimethylformamide (300 ml.), and 1-(4-chlorobenzyl)-1,2-dihydro-4-methyl-2-oxoquinoline (64.7 g.) was added, followed by diethyl oxalate (55 g.). The mixture was stirred at room temperature for 2.5 hours with occasional external cooling to keep the temperature below 25° C. Ether (2 l.) was added, and the mixture was filtered. The solid residue was washed with ether (500 ml.), and then suspended in dimethylformamide (200 ml.) and acidified to pH 2 by the addition of concentrated hydrochloric acid. The resultant mixture was added to water (3 l.), and the mixture filtered, and the solid residue washed with water (2 l.), drained well, and crystallised from ethanol to give ethyl 1-(4-chlorobenzyl)-1,2-dihydro-2-oxoquinol-4-ylpyruvate, m.p. 180°-182° C.

Workup

  1. temperatureexternal cooling
  2. customthe temperature below 25° C
  3. filtrationthe mixture was filtered
  4. washThe solid residue was washed with ether (500 ml.)
  5. additionacidified to pH 2 by the addition of concentrated hydrochloric acid
  6. additionThe resultant mixture was added to water (3 l.)
  7. filtrationthe mixture filtered
  8. washthe solid residue washed with water (2 l.)
  9. customcrystallised from ethanol

Sources & evidence

ORD record
ord-e612258b74744da1aaed3ac7a4f8b10f
Source dataset
uspto-grants-1980_02
Patent number
US04187310

Reaction notes

Loading…