Tetramethyl orthocarbonate → 3-Hydroxy-2-methoxyquinazolin-4(3H)-one

HRID 64995Notes

Reaction equation

HRID 64995 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][OH:7])=[O:5].[CH3:12][O:13][C:14](OC)(OC)OC>CO>[CH3:12][O:13][C:14]1[N:6]([OH:7])[C:4](=[O:5])[C:3]2[C:2](=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:1]=1

Participants

4

Reactant 2

HCID 74613Tetramethyl orthocarbonateHCID 797212-Aminobenzohydroxamic acid

Product 1

HCID 155827103-Hydroxy-2-methoxyquinazolin-4(3H)-oneYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 22.8 g (0.15 mol) of o-aminobenzohydroxamic acid, 50 ml of methanol and 27.2 g (0.2 mol) of orthocarbonic acid tetramethyl ester was boiled under reflux for 2 hours and was then cooled to 5° C. The product which had crystallized out was filtered off with suction. 17 g (60% of theory) of 2-methoxy-3-hydroxy-3,4-dihyro-4-oxo-quinazoline were obtained in the form of colorless crystals having a melting point of 220° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe product which had crystallized out
  3. filtrationwas filtered off with suction

Sources & evidence

ORD record
ord-0c54b1ea714148a496fa7a4b18046342
Source dataset
uspto-grants-1986_09
Patent number
US04612305

Reaction notes

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