Methanol → HCID 21186700, compound

HRID 1384267Notes

Reaction equation

[Na].Cl[C:3]1[N:8]=[C:7]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:6]2=[CH:5][C:4]=1[C:14]#[N:15].[CH3:16][OH:17]>>[C:14]([C:4]1[CH:5]=[C:6]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:7]2=[N:8][C:3]=1[O:17][CH3:16])#[N:15]

Participants

Reactant 3

HCID 887Methanol2×

HCID 5360545Sodium

HCID 21186724HCID 21186724, compound

Product 1

HCID 21186700HCID 21186700, compoundYield 92.5%

Conditions

Temperature: 60 °C

Procedure

In an atmosphere of argon, metallic sodium (230.0 mg, 0.01 g atom) was dissolved in methanol (10.0 ml) at room temperature, a methanol solution (10.0 ml) of 2-chloro-3-cyano-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine (1.03 g, 5.00 mmol) was added dropwise thereto at the same temperature and then the resulting mixture was stirred at 60° C. for 6 hours. After cooling, methanol was evaporated under reduced pressure, the thus obtained residue was mixed with water and extracted with chloroform, and the resulting organic layer was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate. After evaporation of the solvent under reduced pressure, the resulting residue was purified by a silica gel column chromatography (methylene chloride:hexane=2:1) to obtain the title compound (933.8 mg, 92.5%) as white powder.

Workup

temperatureAfter cooling
custommethanol was evaporated under reduced pressure
additionthe thus obtained residue was mixed with water
extractionextracted with chloroform
washthe resulting organic layer was washed with water and saturated brine in that order
dry with materialdried over anhydrous sodium sulfate
customAfter evaporation of the solvent under reduced pressure
customthe resulting residue was purified by a silica gel column chromatography (methylene chloride:hexane=2:1)

Sources & evidence

ORD record: ord-083e34e5e9ae40a68cd04889137a1d83
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06258829B1

Reaction notes

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