Potassium Permanganate → HCID 23505707, compound

HRID 1884362Notes

Reaction equation

HRID 1884362 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 was 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 was 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-afe7365eb08e480a8c0622d67a0fbdc7
Source dataset
uspto-grants-2004_07
Patent number
US06765006B2

Reaction notes

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