Ethanol → HCID 20488241, compound

HRID 1995342Notes

Reaction equation

HRID 1995342 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:22][NH:23][CH3:24].[CH2:25](O)C>>[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]([CH2:22][N:23]([CH3:25])[CH3:24])[CH2:11][C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 10473Dimethylamine, hydrochlorideHCID 131632302-Benzyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one

Product 1

HCID 20488241HCID 20488241, compound

Procedure

A mixture of 2-benzyl-6-phenyl-4,5-dihydro-3(2H)-pyridazinone (23.9 g) paraformaldehyde (5.0 g), and dimethylamine hydrochloride (8.0 g) in 200 ml of ethanol is heated under reflux for 4 hours. The ethanol is removed by distillation on the rotary evaporator and the residue is rendered basic with ammonium hydroxide solution. This is extracted with dichloromethane. The dichloromethane is concentrated on the rotary evaporator and the residue is chromatographed on silica gel with 2% methanol/chloroform to give 2-benzyl-4-(dimethylaminomethyl)-6-phenyl-4,5-dihydro3(2H)-pyridazinone. This is dissolved in 500 ml of methanol and catalytically hydrogenated at 3 atmospheres pressure over 5% paladium on charcoal. The catalyst is removed by filtration and the methanol is concentrated to give 4-(dimethylaminomethyl)-6-phenyl-4,5-dihydro-3(2H)-pyridazinone. This compound is treated with bromine in acetic acid according to the procedure of Example 1 to give 4-(dimethylaminomethyl)-6-phenyl-3(2H)-pyridazinone.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4 hours
  3. customThe ethanol is removed by distillation on the rotary evaporator
  4. extractionThis is extracted with dichloromethane
  5. concentrationThe dichloromethane is concentrated on the rotary evaporator
  6. customthe residue is chromatographed on silica gel with 2% methanol/chloroform

Sources & evidence

ORD record
ord-4015120d9a8e4fbebda31262b9594939
Source dataset
uspto-grants-1983_09
Patent number
US04404203

Reaction notes

Loading…