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

HRID 2176838Notes

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 2 (27.39 g, >99%) as a white solid.

Workup

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

Sources & evidence

ORD record: ord-e1949a3b08094b4292e118fbc58c591f
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067891B2

Reaction notes

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