Dimethyl Sulfoxide → 5-Formylpyridine-2-carbonitrile

HRID 1798841Notes

Reaction equation

HRID 1798841 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[N:17][CH:18]=1.C(N(CC)CC)C>ClCCl>[CH:12]([C:13]1[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[N:17][CH:18]=1)=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 122519662-Cyano-5-hydroxymethylpyridine

Product 1

HCID 109862635-Formylpyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

1.04 g (8.2 mmol) oxalylchloride are dissolved in 8 ml dichloromethane. At −78° C., 1.28 g (16.4 mmol) dimethylsulfoxide are added dropwise. The solution is stirred at −78° C. for 20 minutes, then 1 g (7.46 mmol) of the compound of Example 2A, dissolved in 7 ml dichloromethane, is added, and stirring at −78° C. is continued for another 2 hours. 3.4 g (33.6 mmol) triethylamine are then added dropwise, and after warming up to room temperature, the mixture is purified by column chromatography (silica, eluent: cyclohexane to cyclohexane/ethyl acetate 2:1).

Workup

  1. additionis added
  2. stirringstirring at −78° C.
  3. waitis continued for another 2 hours
  4. temperatureafter warming up to room temperature
  5. customthe mixture is purified by column chromatography (silica, eluent: cyclohexane to cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-8817070c27594ddab04e3c3916d0160b
Source dataset
uspto-grants-2013_01
Patent number
US08343987B2

Reaction notes

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