3-Cyanopyridine → HCID 178511982, compound

HRID 714419Notes

Reaction equation

HRID 714419 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]#[N:10])[CH:4]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>CS(C)=O>[C:12]1([NH:11][C:9]([C:5]2[CH:4]=[N:3][CH:8]=[CH:7][CH:6]=2)=[NH:10])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 793-CyanopyridineHCID 962WaterHCID 6115AnilineHCID 24758Sodium hydride

Product 1

HCID 178511982HCID 178511982, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (60% in mineral oil, 11.52 g, 288 mmol) was added portion-wise over 30 min to a stirred solution of 3-pyridinecarbonitrile (30 g, 288 mmol) and aniline (26 g, 290 mmol) in dimethylsulfoxide (150 mL) at 10° C. The reaction mixture was allowed to warm to ambient temperature with stirring for 18 h. The reaction mixture was slowly and cautiously poured into water containing crushed ice. The solid that precipitated was filtered, washed with petroleum ether, dissolved in dichloromethane and dried over anhydrous Na2SO4. The volatiles were removed under reduced pressure (high vacuum) and the residue was dried to afford 36.5 g of the title compound as a yellow solid.

Workup

  1. customcrushed ice
  2. customThe solid that precipitated
  3. filtrationwas filtered
  4. washwashed with petroleum ether
  5. dissolutiondissolved in dichloromethane
  6. dry with materialdried over anhydrous Na2SO4
  7. customThe volatiles were removed under reduced pressure (high vacuum)
  8. customthe residue was dried

Sources & evidence

ORD record
ord-4974b453787648d5a44a8ad23827f9a1
Source dataset
uspto-grants-2015_11
Patent number
US09187432B2

Reaction notes

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