Reaction #63461

Reaction equation

6-(3,4-Dihydro-1,4(2H)-benzoxazin-6-yl)-2,3,4,5-tetrahydropyridazin-3-one

triethylamine

3,4-dimethoxybenzoylchloride

→

6-(3,4-Dihydro-4-(3,4-dimethoxyphenylcarbonyl)-1,4(2H)-benzoxazin-6-yl)-2,3,4,5-tetrahydropyridazin-3-one

Solvents

methylene chloride

Conditions

Workup

1. 1
   Temperaturethe mixture heated
2. 2
   Temperatureat reflux for four hours
3. 3
   WashThe solution was washed with sodium bicarbonate solution
4. 4
   Otherevaporated to dryness
5. 5
   OtherThe residue was chromatographed on silica gel eluting with 1:1 ethyl acetate
6. 6
   OtherThe title compound was collected as white needles, mp 207°-208° C.

Procedure

6-(3,4-Dihydro-1,4(2H)-benzoxazin-6-yl)-2,3,4,5-tetrahydropyridazin-3-one was dissolved in methylene chloride and 1.1 equivalent of triethylamine. 1.1 equivalent of 3,4-dimethoxybenzoylchloride was added and the mixture heated at reflux for four hours. The solution was washed with sodium bicarbonate solution and then evaporated to dryness. The residue was chromatographed on silica gel eluting with 1:1 ethyl acetate:ethyl ether. The title compound was collected as white needles, mp 207°-208° C.

Source