Dimethyl Sulfate → 6-[2-(4-Methoxy-phenyl)-vinyl]-pyridine-2-carbonitrile

HRID 1797085Notes

Reaction equation

HRID 1797085 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N+:12]=2[O-])=[CH:5][CH:4]=1.COS(OC)(=O)=O.[C-:25]#[N:26].[Na+]>C(O)(C)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[N:12]=[C:13]([C:25]#[N:26])[CH:14]=[CH:15][CH:16]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 8929Sodium CyanideHCID 695921122-[2-(4-Methoxy-phenyl)-vinyl]-pyridine 1-oxide

Product 1

HCID 695920236-[2-(4-Methoxy-phenyl)-vinyl]-pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Following the general method described in example 2b, 2-[2-(4-methoxy-phenyl)-vinyl]-pyridine 1-oxide was reacted first with dimethylsulfate and then with NaCN. After extraction and crystallization the title compound was obtained as a yellow crystalline material. Mp. 121–122° C. (isopropanol), MS: m/e=236 (M+)

Workup

  1. extractionAfter extraction and crystallization the title compound
  2. customwas obtained as a yellow crystalline material

Sources & evidence

ORD record
ord-4823032ef01440d4b8de2bfb09759748
Source dataset
uspto-grants-2006_04
Patent number
US07034044B2

Reaction notes

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