Hydrochloric Acid → HCID 68603345, compound

HRID 641959Notes

Reaction equation

HRID 641959 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][N:7]([C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:16]([O:18]C)=[O:17])[C:6]2=[O:24].[OH-].[Na+].Cl>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][N:7]([C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:16]([OH:18])=[O:17])[C:6]2=[O:24]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68603399HCID 68603399, compound

Product 1

HCID 68603345HCID 68603345, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred suspension of methyl 3-(6-methoxy-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoate (19.3 g) in a mixture of methanol (650 ml) and water (150 ml) was added 2N NaOH (89 ml) and heated to 70° C. until a clear solution was formed at which point the heating stopped. Stirring was continued for a further 1.5 hours. The pH was adjusted to pH˜1 with 1N HCl and the resultant solid collected by filtration. The solid was dried in vacuo for 16 hours to yield 3-(6-methoxy-4-oxoquinazolin-3(4H)-yl)-4-methylbenzoic acid as a white solid (17.8 g); NMR Spectrum: (DMSOd6) 2.15 (s, 3H), 3.88 (s, 3H), 7.49 (m, 1H), 7.57 (m, 2H), 7.71 (d, 1H), 7.93 (s, 1H), 7.98 (m, 1H), 8.20 (s, 1H); Mass Spectrum: M+H+ 311.

Workup

  1. customwas formed at which point the heating
  2. filtrationthe resultant solid collected by filtration
  3. customThe solid was dried in vacuo for 16 hours

Sources & evidence

ORD record
ord-81309007e4e54c84a7ccc28de69b4363
Source dataset
uspto-grants-2010_04
Patent number
US07696215B2

Reaction notes

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