Sodium hydride → HCID 23471585, compound

HRID 128016Notes

Reaction equation

HRID 128016 reaction equation
[CH3:1][CH:2]1[C:7]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13](=[O:19])[CH2:12][C:11]3([CH3:21])[CH3:20])=[N:6][NH:5][C:4](=[O:22])[CH2:3]1.[H-].[Na+].[O:25]1[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][Cl:33])[CH2:27][CH2:26]1>CN(C)C=O>[ClH:33].[CH3:1][CH:2]1[C:7]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13](=[O:19])[CH2:12][C:11]3([CH3:21])[CH3:20])=[N:6][N:5]([CH2:32][CH2:31][N:28]2[CH2:29][CH2:30][O:25][CH2:26][CH2:27]2)[C:4](=[O:22])[CH2:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 767274-(2-Chloroethyl)morpholineHCID 23471600HCID 23471600, compound

Product 1

HCID 23471585HCID 23471585, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3 g of 6-(5-methyl-3-oxo-2,3,4,5-tetrahydropyridazin-6-yl)-1,4,4-trimethyl-1,2,3,4-tetrahydroquinolin-2-one in 30 ml of dimethylformamide was added 0.9 g of 50% sodium hydride. After stirring for about 30 minutes, 1.7 g of 2-morpholinoethyl chloride was added and the mixture was stirred at about 50° C. for one hour. The reaction mixture was poured into 200 ml of ice-cold water and extracted with 150 ml of chloroform. The extract was dried over potassium carbonate and concentrated under reduced pressure. To the residue was added alcoholic hydrogen chloride and the precipitated crystals were filtered off. Recrystallization from isopropanol gave 2.5 g of 6-[5-methyl-2-(2-morpholinoethyl)-3-oxo-2,3,4,5-tetrahydropyridazin-6-yl]-1,4,4-trimethyl-1,2,3,4-tetrahydroquinolin-2-one hydrochloride, melting at 243°-246° C.

Workup

  1. stirringthe mixture was stirred at about 50° C. for one hour
  2. extractionextracted with 150 ml of chloroform
  3. dry with materialThe extract was dried over potassium carbonate
  4. concentrationconcentrated under reduced pressure
  5. additionTo the residue was added alcoholic hydrogen chloride
  6. filtrationthe precipitated crystals were filtered off
  7. customRecrystallization from isopropanol

Sources & evidence

ORD record
ord-ad96d27c692643939cac2c99b4b01f9c
Source dataset
uspto-grants-1981_03
Patent number
US04258185

Reaction notes

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