Pyridine → 2,8-Dimethyl-3H-quinazolin-4-one

HRID 850060Notes

Reaction equation

HRID 850060 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].N1C=CC=[CH:14][CH:13]=1.C(Cl)(=O)C>C1COCC1>[CH3:13][C:14]1[NH:6][C:4](=[O:5])[C:3]2[C:2](=[C:10]([CH3:11])[CH:9]=[CH:8][CH:7]=2)[N:1]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 142218072-Amino-3-methylbenzamide

Product 1

HCID 1354635742,8-Dimethyl-3H-quinazolin-4-oneYield 81.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-amino-3-methylbenzamide (0.5 g, 3.3 mmol) (prepared by conventional methods) and pyridine (0.35 ml, 4.3 mmol) in dry THF (15 ml), was added a solution of acetyl chloride (0.36 ml, 5.0 mmol) in THF (2 ml) dropwise, and the mixture was stirred overnight under nitrogen. The solvent was removed under vacuum and the remaining white slurry was resuspended in 2% aqueous sodium hydroxide solution and neutralised with aqueous hydrochloric acid, whereupon a white precipitate formed. The solid was collected and recrystallised from methanol-water to furnish the required quinazolinone (0.47 g, 81%) m.p. 217-220° C.;

Workup

  1. customThe solvent was removed under vacuum
  2. customformed
  3. customThe solid was collected
  4. customrecrystallised from methanol-water

Sources & evidence

ORD record
ord-19021a7f27d049468bd3f74bdd515263
Source dataset
uspto-grants-2000_01
Patent number
US06015827

Reaction notes

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