Butyl bromide → 1-Butyl-4-methoxy-2-oxo-1,2-dihydro-pyridine-3-carbonitrile

HRID 2401672Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][NH:6][C:5](=[O:9])[C:4]=1[C:10]#[N:11].Br[CH2:13][CH2:14][CH2:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:13]([N:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([C:10]#[N:11])[C:5]1=[O:9])[CH2:14][CH2:15][CH3:16]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 4-methoxy-2-oxo-1,2-dihydro-pyridine-3-carbonitrile (20 g, 133 mmol) in acetonitrile (800 ml) were added 1-bromobutane (15.8 ml, 146 mmol) and potassium carbonate (36.7 g, 266 mmol) and the mixture was heated at 110° C. for 24 hours. The mixture was cooled to room temperature and the solid was filtered off The filtrate was evaporated till dryness and the resulting crude residue was then triturated with diethylether to yield pure intermediate 4 (27.39 g, >99%) as a white solid.

Workup

temperatureThe mixture was cooled to room temperature
filtrationthe solid was filtered off The filtrate
customwas evaporated till dryness
customthe resulting crude residue was then triturated with diethylether

Sources & evidence

ORD record: ord-1a8369019d2540beba89388b8270ad47
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796311B2

Reaction notes

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