DDQ CHCl3 → 4(1H)-Quinazolinone

HRID 635517Notes

Reaction equation

HRID 635517 reaction equation
CO[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][NH:7][C:6]2=[O:13].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.C(Cl)(Cl)Cl>>[N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:12][CH:11]=2)[C:6](=[O:13])[NH:7][CH:8]=1

Participants

3

Reactant 2

HCID 86756416DDQ CHCl3HCID 1354514236-Methoxyquinazolin-4-OL

Product 1

HCID 1354087534(1H)-QuinazolinoneYield 36.5%

Procedure

The Dihydro-(2H)-2-[3-(4-methoxyphenoxy)phenyl]-3-)4-trifluoromethyl benzyl)-6-methoxyquinazoline-4-one, above, was treated with 1.0 mL (0.05 mmol) of 0.05 molar DDQ/CHCl3 suspension and the mixture shaken at room temperature for 3.5-4 hr. The oxidation product was then purified by resin capture (with about 80 mg of VHL aminomethyl polystyrene resin) overnight. The reaction flask was covered with Teflon film. The resin solution was filtered through 30-50 mg of silica gel, washed with 0.5 mL of chloroform. The product was further purified by Prep TLC eluted with 30% ethyl acetate-hexane to give 9.5 mg (36.5%) of the subject quinazolin-4-one as a white solid. 1H-NMR (300 MHz, CDCl3) δ3.82 (s, 3 H), 3.96 (s, 3 H), 5.33 (s, 2 H), 6.80-7.73 (m, 15 H). MS m/z 533 (M+H, 100%).

Workup

  1. customThe oxidation product was then purified by resin capture (with about 80 mg of VHL aminomethyl polystyrene resin) overnight
  2. filtrationThe resin solution was filtered through 30-50 mg of silica gel
  3. washwashed with 0.5 mL of chloroform
  4. customThe product was further purified by Prep TLC
  5. washeluted with 30% ethyl acetate-hexane

Sources & evidence

ORD record
ord-efd06b4968f84a34b1d2bf862caddc32
Source dataset
uspto-grants-2001_02
Patent number
US06187923B1

Reaction notes

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