4-Pyridinecarboxaldehyde → HCID 50885249, compound

HRID 250196Notes

Reaction equation

HRID 250196 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[CH3:9][C:10]1([CH3:18])[O:17][C:15](=[O:16])[CH2:14][C:12](=[O:13])[O:11]1.N1CCC[C@H]1C(O)=O>C(#N)C>[CH3:9][C:10]1([CH3:18])[O:17][C:15](=[O:16])[C:14](=[CH:7][C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[C:12](=[O:13])[O:11]1

Participants

5

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 145742L-Proline

Product 1

HCID 50885249HCID 50885249, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Pyridine-4-carboxaldehyde (2.04 g) was mixed with Meldrum's acid (2,2-Dimethyl-[1,3]dioxane-4,6-dione, 2.7 g) and proline (0.20 g) in acetonitrile (40 ml) with stirring under a nitrogen atmosphere. Almost immediately product began to precipitate. The mixture was stirred overnight, filtered and washed with ether, affording 3.7 g of 2,2-dimethyl-5-pyridin-4-ylmethylene-[1,3]dioxane-4,6-dione which was used with no further purification in the next step.

Workup

  1. customto precipitate
  2. stirringThe mixture was stirred overnight
  3. filtrationfiltered
  4. washwashed with ether

Sources & evidence

ORD record
ord-f40e5f44de4f4a8ab05e2c1c3414bdac
Source dataset
uspto-grants-2011_01
Patent number
US07863305B2

Reaction notes

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