Hydrochloric Acid → 4-Methyl-3-[6-(4-morpholinylmethyl)-4-oxo-3(4H)-quinazolinyl]benzoic acid

HRID 641991Notes

Reaction equation

HRID 641991 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[N:12]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:23][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:19]=2)[N:14]=[CH:13]1.[OH-].[Na+].Cl>CO.O>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N:12]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:23][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[CH:19]=2)[N:14]=[CH:13]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68515979HCID 68515979, compound

Product 1

HCID 685167144-Methyl-3-[6-(4-morpholinylmethyl)-4-oxo-3(4H)-quinazolinyl]benzoic acidYield 100.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 4-methyl-3-[6-(morpholin-4-ylmethyl)-4-oxoquinazolin-3(4H)-yl]benzoate (0.62 g) in methanol (10 ml) and water (4 ml) was added 2N NaOH (2.35 ml) and stirred at room temperature for 4 hours. 1N HCl was added and the reaction was allowed to stand for 16 hours and then concentrated. The residue was dissolved in methanol (40 ml), inorganics removed by filtration. The filtrate concentrated to give 4-methyl-3-[6-(morpholin-4-ylmethyl)-4-oxoquinazolin-3(4H)-yl]benzoic acid as a solid (0.60 g). Mass Spectrum: M+H+ 380.

Workup

  1. waitto stand for 16 hours
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in methanol (40 ml)
  4. custominorganics removed by filtration
  5. concentrationThe filtrate concentrated

Sources & evidence

ORD record
ord-0015576713cc42e1b696593d5d9f3cc8
Source dataset
uspto-grants-2010_04
Patent number
US07696215B2

Reaction notes

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