Methanol → HCID 178497556, compound

HRID 578649Notes

Reaction equation

HRID 578649 reaction equation
[OH: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][N:3]=1.CO.OS(O)(=O)=O.[C:22]([O-])(O)=O.[Na+]>O>[OH: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][N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 178524225HCID 178524225, compound

Product 1

HCID 178497556HCID 178497556, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A 1 L round bottom flask was charged with 4-hydroxyquinazoline-8-carboxylic acid (A), MeOH (300 mL), and H2SO4 (10 mL). The reaction was heated to 50° C. for 2 days. Upon cooling to room temperature, the reaction mixture was neutralized with NaHCO3 and diluted with water. The methanol was removed in vacuo, and the precipitate was collected, washed with water and heptanes, then dried to give methyl 4-hydroxyquinazoline-8-carboxylate (18.3 g, 65%, over 2 steps combining both isomers from A and B).

Workup

  1. temperatureUpon cooling to room temperature
  2. customThe methanol was removed in vacuo
  3. customthe precipitate was collected
  4. washwashed with water and heptanes
  5. customdried

Sources & evidence

ORD record
ord-a2b830db1cea4634a6ae36033b97bf36
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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