Hydroxyamine hydrochloride → 6-chloro-1-methyl-4-phenyl-2(1H)quinazolinone 3-oxide

HRID 128028Notes

Reaction equation

HRID 128028 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7](=[O:13])[N:6](C)[C:5]2(O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl.N[OH:24]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7](=[O:13])[N+:6]([O-:24])=[C:5]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 23471631HCID 23471631, compound

Product 1

HCID 234716266-chloro-1-methyl-4-phenyl-2(1H)quinazolinone 3-oxideYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 3.03 g (0.01 mole) of 6-chloro-3,4-dihydro-4-hydroxy-1,3-dimethyl-4-phenyl-2(1H)-quinazolinone and 2.09 g (0.03 mole) of hydroxylamine hydrochloride in 50 ml of ethanol was refluxed for 5 days. The reaction mixture was cooled, and the solid portion was collected on a filter, washed with ethanol, and dried in air to give 1.75 g (61%) of 6-chloro-1-methyl-4-phenyl-2-(1H)-quinazolinone 3-oxide as yellow crystals: mp 289°-291°; 1H nmr (TFA) δ4.22 ppm (s, 3H) and 7.6-8.5 ppm (m, 8H).

Workup

  1. temperaturewas refluxed for 5 days
  2. temperatureThe reaction mixture was cooled
  3. customthe solid portion was collected on a filter
  4. washwashed with ethanol
  5. customdried in air

Sources & evidence

ORD record
ord-289c0d1915334abb8f9d70a4e817e3bd
Source dataset
uspto-grants-1981_03
Patent number
US04258187

Reaction notes

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