Ammonia hydroxide → 6-Chloro-2-isopropenyl-3H-quinazolin-4-one

HRID 555258Notes

Reaction equation

HRID 555258 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][C:12](=O)[C:13]([CH3:15])=[CH2:14])=[C:6]([CH:10]=1)[C:7]([NH2:9])=[O:8].[OH-].N>CCO>[Cl:1][C:2]1[CH:10]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:11]=[C:12]([C:13]([CH3:15])=[CH2:14])[NH:9][C:7]2=[O:8]

Participants

4

Reactant 2

HCID 21862953Ammonia hydroxideHCID 589496945-Chloro-2-(2-methyl-acryloylamino)-benzamide

Product 1

HCID 1358145016-Chloro-2-isopropenyl-3H-quinazolin-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Chloro-2-(2-methyl-acryloylamino)-benzamide (1.5 mmoL) in EtOH (10 mL) was treated with ammonia hydroxide (˜3.0 mmoL) at 80° C. for 4 h. The reaction was then cooled down and the solvent was removed. The reaction mixture was then partitioned between DCM and water. The organic layer was washed with sat. NH4Cl, brine, dried over anhydrous Na2SO4, filtered, concentrated and purified by silica gel column chromatography to afford the title compound as a white solid.

Workup

  1. temperatureThe reaction was then cooled down
  2. customthe solvent was removed
  3. customThe reaction mixture was then partitioned between DCM and water
  4. washThe organic layer was washed with sat. NH4Cl, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-17d31de3cfe84c03a5e1894424813b1b
Source dataset
uspto-grants-2011_11
Patent number
US08053441B2

Reaction notes

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