Isopropyl Acetate → 2,3-Diethyl 2,3-pyridinedicarboxylate

HRID 907466Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:2]=1.[CH:12]([O:15][C:16](C)=[O:17])(C)[CH3:13]>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]=1[C:16]([O:15][CH2:12][CH3:13])=[O:17]

Participants

Reactant 2

HCID 7915Isopropyl Acetate

HCID 69188Ethyl Nicotinate

Product 1

HCID 108895172,3-Diethyl 2,3-pyridinedicarboxylate

Procedure

To a suspension of 2,3-pyridinedicarboxylic acid (200 g, 1.2 mol) in ethanol (800 ml) was added conc H2SO4 (100 ml) and this mixture was heated to reflux for 3 days (mechanical stirring). It was then cooled down to r.t. and added to crushed ice. Conc NH4OH (405 ml) was then added slowly and the pH was adjusted to 9 by addition of some aq. NH4Cl. The products were extracted into i-PrOAc, dried over Na2SO4 and concentrated to yield 182.48 g of an orange oil containing 88% of the diester (60% yield), 8.1% of ethyl 3-pyridinecarboxylate and 3.5% i-PrOAc. This mixture was used as such in the next step.

Sources & evidence

ORD record: ord-f1d5841bd88c4ed9a57abffb790cb496
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013159B2

Reaction notes

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