Pyridine → HCID 12425344, compound

HRID 322134Notes

Reaction equation

HRID 322134 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 2N HCl (bubbling), separated, washed sequentially with 2×400 mL 2N 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 2N HCl (bubbling)
  3. customseparated
  4. washwashed sequentially with 2×400 mL 2N HCl, brine (400 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3542621c1faa412f8d18e7d2ad9a5a64
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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