2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 23509302, compound

HRID 926550Notes

Reaction equation

HRID 926550 reaction equation
N1CCC[C@H]1C(O)=O.[C:9]([C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=O)#[N:10].[CH3:19][C:20]1([CH3:28])[O:27][C:25](=[O:26])[CH2:24][C:22](=[O:23])[O:21]1.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O>C(O)C>[CH3:19][C:20]1([CH3:28])[O:27][C:25](=[O:26])[CH:24]([CH2:14][C:13]2[CH:12]=[C:11]([CH:18]=[CH:17][CH:16]=2)[C:9]#[N:10])[C:22](=[O:23])[O:21]1

Participants

6

Reactant 4

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 70849Hantzsch esterHCID 90670m-FormylbenzonitrileHCID 145742L-Proline

Product 1

HCID 23509302HCID 23509302, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Proline (0.459 g, 3.95 mmol) was added to a mixture of 3-cyanobenzaldehyde (2.59 g, 19.7 mmol) and Meldrum's acid (2.84 g, 19.7 mmol) in ethanol (200 mL). The mixture was stirred at room temperature for 45 minutes and then diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate (5 g, 20 mmol) was added. The mixture was stirred for an additional hour at room temperature before being concentrated to dryness. The residue was triturated with isopropanol and filtered to provide the title compound as a white solid.

Workup

  1. stirringThe mixture was stirred for an additional hour at room temperature
  2. concentrationbefore being concentrated to dryness
  3. customThe residue was triturated with isopropanol
  4. filtrationfiltered

Sources & evidence

ORD record
ord-ee4900d230f542fc86fdcf1f92aeab1d
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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