Hydrochloric Acid → Quinazoline-6-carboxylic acid

HRID 2079994Notes

Reaction equation

HRID 2079994 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][N:10]=[CH:9]2)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[N:12]1[C:13]2[C:8](=[CH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:15][CH:14]=2)[CH:9]=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58387953HCID 58387953, compound

Product 1

HCID 23130441Quinazoline-6-carboxylic acidYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of quinazoline-6-carboxylic acid ethyl ester (79 mg, 0.391 mmol) in ethanol (4 mL) was added an aqueous solution of 1N sodium hydroxide (4 mL), and the solution was stirred for 1 hour at room temperature. 1N Hydrochloric acid was added to the reaction mixture to adjust the pH to 4, and the solution was evaporated in vacuo. Ethanol was added to the residue, and the organic layer was concentrated. The residue was dissolved in an ethyl acetate-tetrahydrofuran mixture solvent, dried over anhydrous magnesium sulfate, then, evaporated in vacuo, and quinazoline-6-carboxylic acid (15 mg, 0.086 mmol, 22%) was obtained. This was used in the next reaction without purification.

Workup

  1. customthe solution was evaporated in vacuo
  2. additionEthanol was added to the residue
  3. concentrationthe organic layer was concentrated
  4. dissolutionThe residue was dissolved in an ethyl acetate-tetrahydrofuran mixture solvent
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-53d609af32b54d76a0ebd563443d0c09
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…