Tetrahydrofuran → HCID 178498847, compound

HRID 709829Notes

Reaction equation

[C:1]([CH2:3][CH2:4][C:5]1[C:6]([O:15]C)=[N:7][CH:8]=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])#[N:2].[Cl-].[NH+]1C=CC=CC=1.C1COCC1>CN(C=O)C>[C:1]([CH2:3][CH2:4][C:5]1[C:6]([OH:15])=[N:7][CH:8]=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])#[N:2]

Participants

Conditions

Temperature: 100 °C

Procedure

Under a nitrogen atmosphere, to a solution of methyl 5-(2-cyanoethyl)-6-methoxynicotinate (589 mg) in DMF (10 mL) was added pyridinium chloride (3.01 g), and the mixture was stirred at 100° C. for 4 hr. To the reaction mixture was added THF at 0° C., and the resulting precipitate was removed by filtration. The solvent in the filtrate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (479 mg) as white crystals.

Workup

customthe resulting precipitate was removed by filtration
customThe solvent in the filtrate was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-5477a2a01a304d02b7a3ebd0af8d481c
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181186B2

Reaction notes

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