Methanol → Methyl 4-hydroxyquinazoline-6-carboxylate

HRID 1094732Notes

Reaction equation

HRID 1094732 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([OH:14])=[O:13])[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][CH:8]=[C:9]([C:12]([O:14][CH3:19])=[O:13])[CH:10]=2)[N:5]=[CH:4][NH:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 1357038814-Oxo-3,4-dihydroquinazoline-6-carboxylic acid

Product 1

HCID 135742225Methyl 4-hydroxyquinazoline-6-carboxylate

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-oxo-3,4-dihydroquinazoline-6-carboxylic acid (2.5 g, 13.15 mmol) in methanol (80 mL) was added thionyl chloride (2.5 mL) at 5° C. The mixture was refluxed at 80° C. over night. The reaction mixture was concentrated under vacuum and crude taken 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-dihydroquinazoline-6-carboxylate in 55% as solid.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum and crude
  2. washThe organic layer was washed with 10% aqueous NaHCO3, water, brine
  3. customdried
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-82881cdbf81447fa8873b8d585c4e044
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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