P-Anisidine → 5,7-dimethoxy-2-methyl-3-(4-methoxyphenyl)-4(3H)-quinazolinone

HRID 130330Notes

Reaction equation

HRID 130330 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9](=[O:14])O[C:11]([CH3:13])=[N:12][C:7]=2[CH:6]=[C:5]([O:15][CH3:16])[CH:4]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:15][CH3:16])[CH:6]=[C:7]2[C:8]=1[C:9](=[O:14])[N:25]([C:22]1[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=1)[C:11]([CH3:13])=[N:12]2

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 115068145,7-Dimethoxy-2-methyl-4H-benzo[d][1,3]oxazin-4-one

Product 1

HCID 116955305,7-dimethoxy-2-methyl-3-(4-methoxyphenyl)-4(3H)-quinazolinoneYield 13.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 135.5 mg (0.612 mmol) of the benzoxazinone prepared in Example 6 and glacial acetic acid (2 mL), p-anisidine (0.735 mmol) was added and the reaction mixture was heated to 60° C. for 24 hrs. The reaction mixture was concentrated in vacuo and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford the product as a yellow oil (13.7% yield).

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68870afd840442f4b2cb00df645b91ef
Source dataset
uspto-grants-2008_06
Patent number
US07381730B2

Reaction notes

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