Pyridine → HCID 12425344, compound

HRID 396630Notes

Reaction equation

HRID 396630 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-393d8fe9f0c4427f94f1b10b3f1ee0e7
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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