Pyridine → HCID 13469473, compound

HRID 614617Notes

Reaction equation

HRID 614617 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH2:25][OH:26])=[C:5]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].N1C=CC=CC=1.[C:33]1(=[O:39])[O:38][C:36](=[O:37])[CH2:35][CH2:34]1>O1CCOCC1>[CH3:1][C:2]1[NH:3][C:4]([CH2:25][O:26][C:33](=[O:39])[CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[C:5]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7922Succinic anhydrideHCID 13388338HCID 13388338, compound

Product 1

HCID 13469473HCID 13469473, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixed solution of diethyl 2-methyl-4-(2-chlorophenyl)-6-hydroxymethyl-1,4-dihydropyridine-3,5-dicarboxylate (0.3798 g), pyridine (0.791 g) and succinic anhydride (0.1501 g) in dioxane (5 ml) was refluxed for 4.5 hours. The resultant solution was concentrated, acidified with dilute hydrochloric acid and extracted with diethyl ether. The extract was washed with dilute hydrochloric acid and water in turn. The diethyl ether extract was back-extracted with an aqueous saturated sodium bicarbonate solution and the aqueous solution was washed with diethyl ether. The aqueous solution was acidified with dilute hydrochloric acid to precipitate crystals. The crystals were collected by filtration, washed with water and then dried to give diethyl 2-methyl-4-(2-chlorophenyl)-6-(3-carboxypropionyl)oxymethyl-1,4-dihydropyridine-3,5-dicarboxylate (419.3 mg), m.p. 130° to 131° C.

Workup

  1. concentrationThe resultant solution was concentrated
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with dilute hydrochloric acid and water in turn
  4. extractionThe diethyl ether extract
  5. extractionwas back-extracted with an aqueous saturated sodium bicarbonate solution
  6. washthe aqueous solution was washed with diethyl ether
  7. customto precipitate crystals
  8. filtrationThe crystals were collected by filtration
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-568edee8304d45408b268158b4ece74d
Source dataset
uspto-grants-1979_03
Patent number
US04145432

Reaction notes

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