Hydrochloric Acid → 2-(3-Chlorobenzyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylic acid

HRID 422040

Reaction equation

HRID 422040 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][C:6]1[NH:15][C:14](=[O:16])[C:13]2[C:8](=[CH:9][C:10]([C:17]([O:19]C)=[O:18])=[CH:11][CH:12]=2)[N:7]=1.[OH-].[Na+].C(O)C.Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][C:6]1[NH:15][C:14](=[O:16])[C:13]2[C:8](=[CH:9][C:10]([C:17]([OH:19])=[O:18])=[CH:11][CH:12]=2)[N:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 136330125Methyl 2-(3-chlorobenzyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylate

Product 1

HCID 1358172382-(3-Chlorobenzyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylic acidYield 93.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 336 mg of methyl 2-(3-chlorobenzyl)-4-oxo-3,4-dihydroquinazoline-7-carboxylate which was synthesized in Production Example 1, 3.0 mL of aqueous 1N sodium hydroxide solution and 6 mL of ethanol was heated for 2.5 hours under reflux. The reaction solution was allowed to cool off, and to which 3.0 mL of 1N hydrochloric acid and 5 mL of water were added. Whereupon precipitated crystals were recovered by filtration, washed with water and through-flow dried under heating, to provide 300 mg of the title compound.

Workup

  1. temperaturewas heated for 2.5 hours
  2. temperatureunder reflux
  3. temperatureto cool off
  4. customWhereupon precipitated crystals
  5. filtrationwere recovered by filtration
  6. washwashed with water
  7. customthrough-flow dried
  8. temperatureunder heating

Sources & evidence

ORD record
ord-3d5e8ce669e14a9e8fee0c9c62f70618
Source dataset
uspto-grants-2012_01
Patent number
US08101624B2

Linked notes

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