Methanol → Methyl 4-oxo-3,4-dihydroquinazoline-8-carboxylate

HRID 474389Notes

Reaction equation

HRID 474389 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[C:7]([C:12]([OH:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][NH:3]1.S(=O)(=O)(O)O.[OH-].[Na+].[CH3:22]O>>[O:1]=[C:2]1[C:11]2[C:6](=[C:7]([C:12]([O:14][CH3:22])=[O:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][NH:3]1

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 1357422154-Oxo-3,4-dihydroquinazoline-8-carboxylic acid

Product 1

HCID 135742220Methyl 4-oxo-3,4-dihydroquinazoline-8-carboxylateYield 94%

Procedure

4-oxo-3,4-dihydroquinazoline-8-carboxylic acid (5.0 g, 26.3 mmol) was treated with a solution of sulfuric acid ((1.2 equivalents) in anhydrous MeOH (100 mL) under refluxing for 2 days. After cooling to rt, 2N NaOH solution was added to the reaction mixture to adjust pH˜8. After removal of MeOH, methyl ester was collected by filtration, and washing with water and ethyl acetate as pale yellow solid in 94% yield. 1HNMR (in DMSO): 3.84 (s, 3H), 7.42 (t, J=7.6 Hz, 1H), 7.85 (d, J=6.9 Hz, 1H), 8.16 (s, 1H), 8.20 (d, J=7.8 Hz, 1H). Mass: M+H+: 205.

Workup

  1. temperatureunder refluxing for 2 days
  2. customAfter removal of MeOH, methyl ester
  3. filtrationwas collected by filtration
  4. washwashing with water and ethyl acetate as pale yellow solid in 94% yield

Sources & evidence

ORD record
ord-e735c2f18e41448e8c6618bfc64b7151
Source dataset
uspto-grants-2014_01
Patent number
US08637532B2

Reaction notes

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