Pyridine → HCID 12425344, compound

HRID 382687Notes

Reaction equation

HRID 382687 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13](O)(=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].N1C=CC=CC=1.[CH3:28][C:29]1([CH3:37])[O:36][C:34](=[O:35])[CH2:33][C:31](=[O:32])[O:30]1>ClCCl>[CH3:28][C:29]1([CH3:37])[O:36][C:34](=[O:35])[CH:33]([C:13](=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:31](=[O:32])[O:30]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8094Heptanoic AcidHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 12425344HCID 12425344, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Carbonyldiimidazole (71.7 g, 0.442 mol) was added portionwise to a stirred solution of heptanoic acid (0.402 mol) in 300 mL of dry dichloromethane. The resulting mixture was stirred at room temperature for 2 hours. A solution of pyridine (35.8 mL, 0.442 mol) and Meldrum's acid (63.7 g, 0.442 mol) in 150 mL of dry dichloromethane were added over a period of 2 hours to the reaction mixture. The reaction mixture was stirred for 16 hours, quenched with 400 mL of 2 N HCl (bubbling), separated, washed sequentially with 2×400 mL 2 N HCl, brine (400 mL), dried (MgSO4), and the solvent was removed in vacuo to give the title compound as aviscous oil. The crude product was used in the next step after spectral characterization.

Workup

  1. stirringThe reaction mixture was stirred for 16 hours
  2. customquenched with 400 mL of 2 N HCl (bubbling)
  3. customseparated
  4. washwashed sequentially with 2×400 mL 2 N HCl, brine (400 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cd45c138bbde4710953a0f8b10700f48
Source dataset
uspto-grants-2001_10
Patent number
US06310076B1

Reaction notes

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