Cyanoacetamide → 4-Methyl-2-oxo-6-(phenylmethyl)-1,2-dihydro-3-pyridinecarbonitrile

HRID 42483

Reaction equation

[C:1]1([CH2:7][C:8](=O)[CH2:9][C:10](=O)[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14]([CH2:16][C:17]([NH2:19])=[O:18])#[N:15].N1CCCCC1>CCO.O>[CH3:11][C:10]1[NH:19][C:17](=[O:18])[C:16]([C:14]#[N:15])=[C:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:9]=1.[CH3:11][C:10]1[CH:9]=[C:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:19][C:17](=[O:18])[C:16]=1[C:14]#[N:15]

Participants

Conditions

Temperature: 75 °C

Procedure

1-Phenyl-2,4-pentanedione (18.32 g, 104 mmol) and cyanoacetamide (8.74 g, 104 mmol) were dissolved in EtOH (104 mL) and heated until homogenous (ca. 75° C.). Piperidine (8.86 g, 104 mmol) was added and the reaction mixture heated at reflux for 15-30 min. followed by cooling to room temperature, during which time precipitation occurred. The heterogenous contents were filtered to give a solid which was suspended in 200 mL water and stirred vigorously for 20 min. The heterogenous mixture was filtered to afford 6-methyl-2-oxo-4-(phenylmethyl)-1,2-dihydro-3-pyridinecarbonitrile and 4-methyl-2-oxo-6-(phenylmethyl)-1,2-dihydro-3-pyridinecarbonitrile (12.06 g, 52%). LCMS MH+=225.1

Workup

temperaturethe reaction mixture heated
temperatureat reflux for 15-30 min.
temperatureby cooling to room temperature, during which time precipitation
filtrationThe heterogenous contents were filtered
customto give a solid which
filtrationThe heterogenous mixture was filtered

Sources & evidence

ORD record: ord-4a5291a1843c4cf5bf4c5ef412c25408
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536179B2

Linked notes

Loading…