Sodium Cyanide → HCID 90112398, compound

HRID 1508870Notes

Reaction equation

HRID 1508870 reaction equation
CS(O[CH2:6][C:7]1[CH:8]=[N:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=1)(=O)=O.[C-:15]#[N:16].[Na+]>C(#N)C>[CH3:14][O:13][CH:10]1[NH:9][CH:8]=[C:7]([CH2:6][C:15]#[N:16])[CH:12]=[CH:11]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 58213827HCID 58213827, compound

Product 1

HCID 90112398HCID 90112398, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (6-methoxypyridin-3-yl)methyl methanesulfonate (1.4 g, 6.14 mmol) in acetonitrile (13 mL) was treated with sodium cyanide (0.752 g, 15.3 mmol) dropwise and the reaction mixture was heated at reflux for 48 h. After this time, the reaction was cooled and concentrated. The residue was purified by column chromatography (silica, hexanes/ethyl acetate) to afford the title compound (0.800 g, 57%) as a white solid. MW=150.18. 1H NMR (CD3OD, 300 MHz) δ 8.12-8.09 (m, 1H), 7.68 (dd, J1=10.9 Hz, h=2.4 Hz, 1H), 6.82 (d, J=8.6 Hz, 1H), 4.86 (s, 1H), 3.90 (s, 3H), 3.85 (s, 2H); APCI MS m/z 151 [M+H]+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 48 h
  3. temperatureAfter this time, the reaction was cooled
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (silica, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-fb95511b497f4ca4b7e1cf06bd419a8a
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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