Dimethyl Sulfate → 6-(2-p-Tolyl-vinyl)-pyridine-2-carbonitrile

HRID 965853

Reaction equation

HRID 965853 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N+:10]=2[O-])=[CH:3][CH:2]=1.COS(OC)(=O)=O.[C-:24]#[N:25].[Na+]>C(O)(C)C>[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]2[N:10]=[C:11]([C:24]#[N:25])[CH:12]=[CH:13][CH:14]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 8929Sodium CyanideHCID 695921292-(2-p-Tolyl-vinyl)-pyridine 1-oxide

Product 1

HCID 695920426-(2-p-Tolyl-vinyl)-pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a variation to the procedure referred to in example 1, 2-(2-p-tolyl-vinyl)-pyridine 1-oxide (9.8 g, 46 mmol) was reacted first with dimethylsulfate ( 5.8 g, 46 mmol) and then with NaCN (2.74 g, 56 mmol). After extraction and crystallization 6-(2-p-tolyl-vinyl)-pyridine-2-carbonitrile (5.8 g, 57%) was obtained as a yellow crystalline material. Mp. 137-138° C. (isopropanol), MS: m/e=220 (M+)

Workup

  1. extractionAfter extraction
  2. customcrystallization 6-(2-p-tolyl-vinyl)-pyridine-2-carbonitrile (5.8 g, 57%)
  3. customwas obtained as a yellow crystalline material

Sources & evidence

ORD record
ord-4f80f94ca7fb497abb25fde0d2a3ffae
Source dataset
uspto-grants-2005_10
Patent number
US06951875B2

Linked notes

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