Water → 2-Cyano-4-methylpyridin-1-ium-1-olate

HRID 1780894Notes

Reaction equation

HRID 1780894 reaction equation
[N+:1]1([O-:8])[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.[Si]([C:13]#[N:14])(C)(C)C.CN(C)C(Cl)=O.O>C(Cl)Cl>[C:13]([C:2]1[CH:3]=[C:4]([CH3:7])[CH:5]=[CH:6][N+:1]=1[O-:8])#[N:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6598Dimethylcarbamoyl ChlorideHCID 138574-Picoline N-oxideHCID 82115Trimethylsilyl cyanide

Product 1

HCID 37251652-Cyano-4-methylpyridin-1-ium-1-olate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-picoline-N-oxide (20 g) in CH2Cl2 (360 mL) was added TMSCN (26.5 mL), stirred 5 minutes, added dimethyl carbamyl chloride (16.6 mL) was added slowly dropwise. The mixture was stirred at RT overnight, poured onto 400 mL H2O, and 40 g NaCO3. Separation of layers and evaporation of CH2Cl2 gave 17.25 g of 2-Cyano-4-methylpyridine-N-oxide, recrystallized from hexane, m.p. 95°-98° C.

Workup

  1. additionwas added slowly dropwise
  2. stirringThe mixture was stirred at RT overnight
  3. customSeparation of layers and evaporation of CH2Cl2

Sources & evidence

ORD record
ord-07125b3137d04172940ec927c0ba18f5
Source dataset
uspto-grants-1997_05
Patent number
US05631264

Reaction notes

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