Methanol → methyl 4-oxo-3,4-dihydroquinazoline-7-carboxylate

HRID 1094729Notes

Reaction equation

HRID 1094729 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][NH:3]1.S(Cl)(Cl)=O.[CH3:19]O>>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:19])=[O:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][NH:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 1354835884-Oxo-3,4-dihydroquinazoline-7-carboxylic acid

Product 1

HCID 135481487methyl 4-oxo-3,4-dihydroquinazoline-7-carboxylateYield 70%

Conditions

Temperature
80 °C

Procedure

A mixture of 4-oxo-3,4-dihydroquinazoline-7-carboxylic acid (2.5 g, 13.15 mmol) in 80 mL of methanol was added thionyl chloride (2.5 mL) at 5° C. and then refluxed at 80° C. over night. The reaction mixture was concentrated under vacuum and the residue dissolved in ethyl acetate. The organic layer was washed with 10% aqueous NaHCO3, water, brine and dried. The solvent was removed to give methyl 4-oxo-3,4-dihydroquinazoline7-carboxylate in 70% yield as solid.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThe organic layer was washed with 10% aqueous NaHCO3, water, brine
  4. customdried
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-0a1d9585bb244b4c98c9a46503e503e7
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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