Hydrogen Sulfide → Ethyl 2-methyl-4-phenylpyridine-3-carboxylate

HRID 1164821Notes

Reaction equation

HRID 1164821 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[S].S>C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 402Hydrogen SulfideHCID 5362487SulfurHCID 14652661Ethyl 2-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylate

Product 1

HCID 14652662Ethyl 2-methyl-4-phenylpyridine-3-carboxylateYield 79.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.32 mol ethyl 1,4-dihydro-2-methyl-4-phenyl-3-pyridinecarboxylate in 50 ml of methylene chloride was added 16 g (0.5 mol) of sulfur. The temperature of the well-stirred dark solution was raised over a period of about 30 minutes to 170°-180° C. When the development of hydrogen sulfide had subsided, the reaction mixture was cooled to room temperature, taken up in toluene, and filtered through Celite filter aid. The filtrate was concentrate under vacuum and the residue chromatographed on silica gel, eluting with ethyl acetate/hexane to yield 61.7 g of ethyl 2-methyl-4-phenyl-3-pyridinecarboxylate.

Workup

  1. temperatureThe temperature of the well-stirred dark solution was raised over a period of about 30 minutes to 170°-180° C
  2. filtrationfiltered through Celite
  3. filtrationfilter aid
  4. concentrationThe filtrate was concentrate under vacuum
  5. customthe residue chromatographed on silica gel
  6. washeluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-7a3c4c64575a4aa8900b87db438e22b7
Source dataset
uspto-grants-1990_03
Patent number
US04906624

Reaction notes

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