Ethyl Nicotinate → AGN-PC-0NI5SB

HRID 1953040Notes

Reaction equation

HRID 1953040 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1>[Pd]>[N:4]1[CH:3]=[C:2]([C:1]([O:9][CH2:10][CH3:11])=[O:8])[CH:7]=[CH:6][C:5]=1[C:5]1[CH:6]=[CH:7][C:2]([C:1]([O:9][CH2:10][CH3:11])=[O:8])=[CH:3][N:4]=1

Participants

3

Reactant 1

HCID 69188Ethyl Nicotinate

Product 1

HCID 12227215AGN-PC-0NI5SB

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Diethyl bipyridine-5,5'-dicarboxylate was prepared from catalytic dehydrogenative coupling reaction of ethyl nicotinate (Aldrich Chemical Co., 51.2 g.) in the presence of 10% Pd/C (Fluka, 15 g.) in a sealed tube at 135-140° C. for 4-7 days according to reported procedure. Subsequent recrystallization from isopropanol afforded the product as off-white needles. M.p. 148-149° C. Yield 12.1 g. (26%). Anal. Calcd for C16H16N2O4 : C, 63.99; H, 5.37; N, 9.33. Found: C, 64.04; H, 5.16; N, 9.05.

Workup

  1. customSubsequent recrystallization from isopropanol

Sources & evidence

ORD record
ord-2873789ae2544abbb9a3fd851567ca94
Source dataset
uspto-grants-2000_09
Patent number
US06114498

Reaction notes

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