Acetone → ST001233

HRID 1774292Notes

Reaction equation

HRID 1774292 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][C:10]([CH3:12])=O.[C:13](#[N:17])[CH2:14][C:15]#[N:16].C([O-])(=O)C.[NH4+:22]>>[NH2:16][C:15]1[N:22]=[C:10]([CH3:12])[CH:9]=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:14]=1[C:13]#[N:17]

Participants

5

Reactant 4

HCID 180AcetoneHCID 240BenzaldehydeHCID 8010MalononitrileHCID 517165Ammonium Acetate

Product 1

HCID 610514ST001233Yield 40%

Procedure

Benzaldehyde (406 μl, 4 mmol), acetone (294 μl, 4 mmol), malononitrile (264 mg, 4 mmol) e ammonium acetate (462 mg, 6 mmol) were placed in a microwave tube and irradiated with microwaves (Solvent: none; Power: 150 W; Ramp time: 5 min; Heating time: 10 min; Temperature: 100° C.; Pressure: 175 psi; Stirring: on; Cooling: on). At the end of the microwave irradiation cycle, the solvent was removed under reduced pressure. The crude product was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate=90/10) to obtain 2-amino-4-phenyl-6-methylnicotinonitrile in 40% yield.

Workup

  1. customirradiated with microwaves (Solvent: none; Power: 150 W; Ramp time: 5 min; Heating time: 10 min; Temperature: 100° C.; Pressure: 175 psi; Stirring: on; Cooling: on)
  2. customAt the end of the microwave irradiation cycle
  3. customthe solvent was removed under reduced pressure
  4. customThe crude product was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate=90/10)

Sources & evidence

ORD record
ord-745ca3445bb7414c8101155f63f43a98
Source dataset
uspto-grants-2016_02
Patent number
US09260394B2

Reaction notes

Loading…