Formaldehyde → 1-isopropyl-7-methyl-4-(m-methoxyphenyl)-2(1H)-quinazolinone

HRID 1834760Notes

Reaction equation

HRID 1834760 reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:14])[CH:12]=2)[CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[NH:6][C:5]1=[O:23])([CH3:3])[CH3:2].[Mn]([O-])(=O)(=O)=O.[K+].C=O>O1CCOCC1.O.C1C=CC=CC=1>[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:14])[CH:12]=2)[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[N:6][C:5]1=[O:23])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 712FormaldehydeHCID 516875Potassium PermanganateHCID 203719553,4-dihydro-1-isopropyl-4-(3-methoxyphenyl)-7-methyl-2(1H)-quinazolinone

Product 1

HCID 46200211-isopropyl-7-methyl-4-(m-methoxyphenyl)-2(1H)-quinazolinone

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

1.555 g of 3,4-dihydro-1-isopropyl-4-(3-methoxyphenyl)-7-methyl-2(1H)-quinazolinone in 40 ml of p-dioxane is charged to a vessel having a dropping funnel, agitation means and thermometer. The charged vessel is cooled in a water bath (running water at 14°); a slution of 0.88 g of potassium permanganate in 20 ml of water is placed in the dropping funnel, which is then added dropwise to the vessel with stirring during which temperatures range from 15° to 18°). The reaction mixture is then allowed to rise to room temperature (26°), at which is stirred for 2 hr. 20 min. 0.38 ml of aqueous formaldehyde (37%) is then added, and the mixture stirred for 10 minutes. The mixture is then filtered through celite (diatomaceous earth), and the filtrate retained. The filter cake is then washed with 75 ml of water/p-dioxane (20:15), the washings and filtrate are combined, extracted four times with 20 ml portions methylenechloride. The combined extracts are then evaporated to dryness to obtain a residue which is taken up in 100 ml benzene, 100 ml of petroleum ether added thereto, the solution filtered through 0.5 g of charcoal, (at room temperature) and then evaporated to dryness to obtain 1-isopropyl-4-(3-methoxyphenyl)-7-methyl-2(1H)-quinazolinone.

Workup

  1. additionis then added dropwise to the vessel
  2. customrange from 15° to 18°
  3. customto rise to room temperature
  4. custom(26°)
  5. stirringat which is stirred for 2 hr
  6. custom20 min
  7. stirringthe mixture stirred for 10 minutes
  8. filtrationThe mixture is then filtered through celite (diatomaceous earth)
  9. washThe filter cake is then washed with 75 ml of water/p-dioxane (20:15)
  10. extractionextracted four times with 20 ml portions methylenechloride
  11. customThe combined extracts are then evaporated to dryness
  12. customto obtain a residue which
  13. filtrationthe solution filtered through 0.5 g of charcoal, (at room temperature)
  14. customevaporated to dryness

Sources & evidence

ORD record
ord-f16c7e85907e4e8aa1807449a11b29fd
Source dataset
uspto-grants-1978_01
Patent number
US04071516

Reaction notes

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