Acetic Acid → HCID 15913004, compound

HRID 2184723Notes

Reaction equation

HRID 2184723 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[O:8])[CH:2]=1.[C-]#N.[Na+].[C:12]([O:16][CH3:17])(=[O:15])[CH:13]=[CH2:14].C(O)(=O)C>CN(C)C=O.O>[O:8]=[C:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH2:14][CH2:13][C:12]([O:16][CH3:17])=[O:15]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7294Methyl AcrylateHCID 8929Sodium CyanideHCID 103713-Pyridinecarboxaldehyde

Product 1

HCID 15913004HCID 15913004, compoundYield 22.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

A solution of 3-pyridinecarboxaldehyde (10.7 g) in dimethyl formamide (DMF, 20 mL) was added over 10 min. to a stirred solution of sodium cyanide (2.45 g) in DMF (80 mL) at room temperature under dry nitrogen. The solution was stirred for 30 min. and methyl acrylate (18.6 g) in DMF (80 mL) was added dropwise over 50 min. The reaction mixture was stirred for 3 h. Acetic acid (6.6 mL) and water (30 mL) were added and stirring was continued for 5 minutes. The mixture was concentrated, dissolved in water (360 mL), and pH was adjusted to 7.5 with sodium bicarbonate. The aqueous layer was extracted with chloroform (3×300 mL). The chloroform layers were combined, washed with saturated sodium chloride solution (brine), dried (MgSO4), filtered, concentrated and purified by flash chromatography (SiO2, 30% ethyl acetate in hexanes) to yield 4.3 g (22%) of the title compound; ESMS (M+1)+194.

Workup

  1. stirringThe reaction mixture was stirred for 3 h
  2. stirringstirring
  3. waitwas continued for 5 minutes
  4. concentrationThe mixture was concentrated
  5. dissolutiondissolved in water (360 mL)
  6. extractionThe aqueous layer was extracted with chloroform (3×300 mL)
  7. washwashed with saturated sodium chloride solution (brine)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified by flash chromatography (SiO2, 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-937cd0006b934186a6ad5c72d6be0460
Source dataset
uspto-grants-2002_06
Patent number
US06399606B1

Reaction notes

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