6-chloro-4-hydroxy-3-methyl-4-phenyl-1H-quinazolin-2-one → HCID 178518621, compound

HRID 128024Notes

Reaction equation

HRID 128024 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[N:6](C)[C:5]2(O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.N[OH:23]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[N+:6]([O-:23])=[C:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 3200296-chloro-4-hydroxy-3-methyl-4-phenyl-1H-quinazolin-2-oneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 178518621HCID 178518621, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 86.6 g (0.3 mole) of 6-chloro-3,4-dihydro-4-hydroxy-3-methyl-4-phenyl-2(1H)-quinazolinone and 62.5 g (0.9 mole) of hydroxylamine hydrochloride in 1500 ml ethanol was refluxed for 187 hr, and then cooled. The solid portion of the reaction mixture was collected on a filter, washed with ethanol, and dried in air to give 67.9 g (83%) of 6-chloro-4-phenyl-2(1H)-quinazolinone 3-oxide as yellow crystals: mp 267°-269°.

Workup

  1. temperaturewas refluxed for 187 hr
  2. temperaturecooled
  3. customThe solid portion of the reaction mixture was collected on a filter
  4. washwashed with ethanol
  5. customdried in air

Sources & evidence

ORD record
ord-5254592c8f054652902ad67dd923cee4
Source dataset
uspto-grants-1981_03
Patent number
US04258187

Reaction notes

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