Ammonium Chloride → 4-Methyl-4-phenyl-3,4-dihydro-1H-quinazolin-2-one

HRID 1497734Notes

Reaction equation

HRID 1497734 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9](=[O:17])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][Mg]Br.[NH4+].[Cl-]>C1COCC1>[CH3:18][C:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9](=[O:17])[NH:8]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 634302(1H)-Quinazolinone, 4-phenyl-HCID 178418573HCID 178418573, compound

Product 1

HCID 1176010134-Methyl-4-phenyl-3,4-dihydro-1H-quinazolin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-Phenyl-1H-quinazolin-2-one (5.0 g, 4.5 mmol) in THF (50 ml) is added methylmagnesium bromide (15.0 ml) dropwise at −78° C. under nitrogen. The mixture is stirred overnight at room temperature. The mixture is poured into an aqueous solution of NH4Cl and then extracted with EtOAc. The organic phase is washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue is purified on silica gel to give product as a white solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase is washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue is purified on silica gel
  7. customto give product as a white solid

Sources & evidence

ORD record
ord-2394edaa774548dda0671e282f6907e3
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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