Potassium Permanganate → HCID 23505707, compound

HRID 991512Notes

Reaction equation

HRID 991512 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]3[O:14][CH2:13][O:12][C:9]=3[CH:10]=2)[CH:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:4][C:3]1=[O:21].[O-][Mn](=O)(=O)=O.[K+]>O1CCOCC1>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]3[O:14][CH2:13][O:12][C:9]=3[CH:10]=2)[C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:4][C:3]1=[O:21]

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 13098806HCID 13098806, compound

Product 1

HCID 23505707HCID 23505707, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-methyl-6,7-methylenedioxy-4-phenyl-3,4-dihydroquinazolin-2(1H)-one (47 mg) in dioxane (3 mL) was added an aqueous solution of KMnO4 (33 mg in 3 mL of water) at 10° C. After the addition, the mixture as extracted with EtOAc (3×10 mL). The organic phase was concentrated in vacuo. To the residue, water (70 mL) was added. The resulting solid was collected by filtration, washed with water, dried in vacuo to provide the title compound as a yellow solid (20 mg, 42%), mp: 253-255° C. 1H NMR (CDCl3): 7.69-7.66 (m, 2H), 7.53-7.51 (m, 3H), 7.18 (s, 1H), 6.86 (s, 1H), 6.11 (s, 2H), 3.76 (s, 3H). Anal. calcd. for C16H12N2O3: C, 68.27; H, 4.32; N, 9.99. Found: C, 67.99; H, 4.17; N, 9.73.

Workup

  1. additionAfter the addition
  2. extractionthe mixture as extracted with EtOAc (3×10 mL)
  3. concentrationThe organic phase was concentrated in vacuo
  4. additionTo the residue, water (70 mL) was added
  5. filtrationThe resulting solid was collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-5f9e40fd4b5141ac98995f40f8a91325
Source dataset
uspto-grants-2002_10
Patent number
US06465472B1

Reaction notes

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