P-Anisidine → 5,7-Dimethoxy-3-(4-methoxyphenyl)quinazoline-4-one

HRID 130328Notes

Reaction equation

HRID 130328 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9](=[O:13])O[CH:11]=[N:12][C:7]=2[CH:6]=[C:5]([O:14][CH3:15])[CH:4]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:14][CH3:15])[CH:6]=[C:7]2[C:8]=1[C:9](=[O:13])[N:24]([C:21]1[CH:22]=[CH:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=1)[CH:11]=[N:12]2

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 115358035,7-Dimethoxy-4H-benzo[d][1,3]oxazin-4-one

Product 1

HCID 116881915,7-Dimethoxy-3-(4-methoxyphenyl)quinazoline-4-oneYield 40%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 200 mg (0.97 mmol) of the benzoxazinone prepared in Example 4 and 119 mg (0.97 mmol) of p-anisidine in 5 ml of xylene was refluxed for 4 hours. The solvent was removed and the target compound purified by flash chromatography on silica gel (loaded with CH2Cl2 and eluted with 40% EtOAc in hexane) to obtain 120 mg of 5,7-dimethoxy-3-(4-methoxyphenyl)-4(3H)-quinazolinone (40% yield) as a white solid.

Workup

  1. temperaturewas refluxed for 4 hours
  2. customThe solvent was removed
  3. customthe target compound purified by flash chromatography on silica gel (loaded with CH2Cl2 and eluted with 40% EtOAc in hexane)

Sources & evidence

ORD record
ord-277d632429dd4186b856db016103cfe7
Source dataset
uspto-grants-2008_06
Patent number
US07381730B2

Reaction notes

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