Sodium Cyanide → 4-Hydroxyquinazoline-6-carbonitrile
Reaction equation
N[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][NH:6][C:5]2=[O:12].N([O-])=O.[Na+].[Cu](C#N)[C:18]#[N:19].[C-]#N.[Na+]>Cl.O>[C:18]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][NH:6][C:5]2=[O:12])#[N:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 5 °C
Procedure
6-Aminoquinazolin-4(3H)-one was slurried in 300 ml of 5% hydrochloric acid and the reaction mixture was cooled to 5° C. A solution of 6.72 g (0.097 mol) of sodium nitrite in 30 ml of water was added dropwise over 2.5 hours while maintaining the reaction temperature below 10° C. The resulting diazonium salt was then added portionwise to a hot (86° C.) solution of 7.84 g (0.0876 mol) of copper cyanide and 11.0 g (0.224 mol) sodium cyanide in 60 ml of water. Evolution of nitrogen was evident throughout the addition. After stirring for 30 minutes, the reaction mixture was filtered, washed with water, and air-dried. The crude product (9.1 g) was purified by silica gel chromatography to afford 3.89 g (26%) of the title compound; m.p. 294°-300° C.
Workup
- temperaturewhile maintaining the reaction temperature below 10° C
- additionEvolution of nitrogen was evident throughout the addition
- filtrationthe reaction mixture was filtered
- washwashed with water
- customair-dried
- customThe crude product (9.1 g) was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-0179a14c29e24d20990bc3830e5680cc
- Source dataset
- uspto-grants-1990_04
- Patent number
- US04920224
Reaction notes
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