Formaldehyde → 5-(1-Methylethyl)-8-phenyl-1,3-dioxolo(4,5-g)quinazolin-6(5H)-one

HRID 1973433Notes

Reaction equation

HRID 1973433 reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]3[O:16][CH2:15][O:14][C:11]=3[CH:12]=2)[CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:6][C:5]1=[O:23])([CH3:3])[CH3:2].O1CCOCC1.[Mn]([O-])(=O)(=O)=O.[K+].C=O>O>[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]3[O:16][CH2:15][O:14][C:11]=3[CH:12]=2)[C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:6][C:5]1=[O:23])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 312751,4-DioxaneHCID 516875Potassium PermanganateHCID 127894691-isopropyl-4-phenyl-6,7-methylenedioxy-3,4-dihydro-2(1H)-quinazolinone

Product 1

HCID 363315-(1-Methylethyl)-8-phenyl-1,3-dioxolo(4,5-g)quinazolin-6(5H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 8.5 gm. of 1-isopropyl-4-phenyl-6,7-methylenedioxy-3,4-dihydro-2(1H)-quinazolinone in 225 ml. of p-dioxane, cooled to 10°-13°C., is added dropwise a solution of 4.3 gm. of potassium permanganate in 185 ml. of water. When the addition is complete, 2 ml. of formalin solution are added. Precipitated solids are removed by filtration and the solvents stripped from the filtrate at reduced pressure. The residue is decolorized with activated charcoal in ethyl acetate and recrystallized from ethyl acetate to obtain 1-isopropyl-4-phenyl-6,7-methylenedioxy-2(1H)-quinazolinone, m.p. 187°-191°C.

Workup

  1. additionis added dropwise a solution of 4.3 gm
  2. additionWhen the addition
  3. customPrecipitated solids
  4. customare removed by filtration
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ecdc4d0b8bb14e558bc49fb202a99d7f
Source dataset
uspto-grants-1976_12
Patent number
US03997564

Reaction notes

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