Reaction #1555

Reaction equation

5,6-diethyl-2-(3-formyl-phenyl)-3-propargyl-4(3H)-pyrimidinone

hydroxylamine hydrochloride

→

5,6-diethyl-2-(3-hydroxyiminophenyl)-3-propargyl-4(3H)-pyrimidinone

Yield 77.6%

5,6-Diethyl-2-(3-hydroxyiminophenyl)-3-propargyl-4(3H)-pyrimidinone

Yield 77.6%

Solvents

ethanol

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was refluxed for 17 hours
2. 2
   OtherThe ethanol was removed in vacuo and ether and ethyl acetate
3. 3
   workup.ADDITIONwere added to the residue
4. 4
   WashThe organics were washed 3 times with water
5. 5
   Filtrationfiltered
6. 6
   Otherto remove 0.22 g of 5,6-diethyl-2-(3-hydroxyiminophenyl)-3-propargyl-4(3H)-pyrimidinone (compound 139)
7. 7
   DryingThe organic layer was dried over MgSO4
8. 8
   Concentrationconcentrated

Procedure

To a 100 mL RBF were charged 1.1 g (3.7 mmol) of 5,6-diethyl-2-(3-formyl-phenyl)-3-propargyl-4(3H)-pyrimidinone, 0.52 g (7.5 mmol) of hydroxylamine hydrochloride and 50 mL of ethanol. The reaction mixture was refluxed for 17 hours. The ethanol was removed in vacuo and ether and ethyl acetate were added to the residue. The organics were washed 3 times with water. The organic layer was gravity filtered to remove 0.22 g of 5,6-diethyl-2-(3-hydroxyiminophenyl)-3-propargyl-4(3H)-pyrimidinone (compound 139). The organic layer was dried over MgSO4 and concentrated to yield a further 0.67 g of 5,6-diethyl-2-(3-hydroxyiminophenyl)-3-propargyl-4(3H)-pyrimidinone (compound 139) as a white solid. A combined yield of 77.6% was obtained. 1H-NMR (CDCl3) 1.25(6H,m); 2.35(1H,t); 2.65(4H,m); 4.6(2H,d); 7.49-8.15(4H,m); 8.7(1H,s)

Source