Hydrochloric Acid → 2-(4-Methylphenyl)quinazolin-4(3H)-one

HRID 1973868Notes

Reaction equation

HRID 1973868 reaction equation
N1C=CC=CC=1.[OH-].[Na+].Cl.C(O)C.[CH3:13][C:14]1[CH:31]=[CH:30][C:17]([C:18]([NH:20][C:21]2[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=2[C:23]([NH2:25])=[O:24])=O)=[CH:16][CH:15]=1>>[CH3:13][C:14]1[CH:31]=[CH:30][C:17]([C:18]2[NH:25][C:23](=[O:24])[C:22]3[C:21](=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:20]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 1049PyridineHCID 14798Sodium HydroxideHCID 8196472-[(4-methylbenzoyl)amino]benzamide

Product 1

HCID 1354521092-(4-Methylphenyl)quinazolin-4(3H)-oneYield 93.1%

Procedure

A mixture of 11 ml of pyridine in 340 ml of 2 normal aqueous sodium hydroxide was heated to the reflux temperature and to the hot solution was added in one portion 16.3 g of 2-(4-methylbenzamido)benzamide. The mixture was maintained at reflux temperature for 15 minutes, then poured into 1000 ml of ice. The cold mixture was acidified with concentrated hydrochloric acid and the precipitate was cooled to give 14.1 g of white 2-(4-methylphenyl)-quinazolin-4(3H)-one, m.p. 242°-243.5° (from ethanol).

Workup

  1. temperaturewas heated to the reflux temperature and to the hot solution
  2. temperatureThe mixture was maintained
  3. temperatureat reflux temperature for 15 minutes
  4. temperaturethe precipitate was cooled

Sources & evidence

ORD record
ord-f55a12b503544866bfe4d9cc4b9cd70a
Source dataset
uspto-grants-1976_12
Patent number
US03998951

Reaction notes

Loading…