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

HRID 128038Notes

Reaction equation

HRID 128038 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]>COCCO>[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 51.3%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A stirred mixture of 2.89 g (0.01 mole) of 6-chloro-3,4-dihydro-4-hydroxy-3-methyl-4-phenyl-2(1H)-quinazolinone and 2.09 g (0.03 mole) of hydroxylamine hydrochloride in 50 ml of 2-methoxyethanol (ethylene glycol monomethyl ether) was refluxed for 2 hours, and then cooled to 0°. The solid that formed was collected on a filter, washed with ethanol, and dried in air to give 1.40 g (51%) of 6-chloro-4-phenyl-2(1H)-quinazolinone 3-oxide as yellow crystals, mp 267°-269°.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperaturecooled to 0°
  3. customThe solid that formed
  4. customwas collected on a filter
  5. washwashed with ethanol
  6. customdried in air

Sources & evidence

ORD record
ord-c4f4edbaf8234c8e845eb35dc0a70160
Source dataset
uspto-grants-1981_03
Patent number
US04258187

Reaction notes

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