Pyridine → HCID 13469473, compound

HRID 894692Notes

Reaction equation

HRID 894692 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-f19e0b385a974745bab6928e2216f13d
Source dataset
uspto-grants-1981_08
Patent number
US04284634

Reaction notes

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