Nicotinic Acid → 3-Pyridinecarboxylic acid, butyl ester

HRID 1530188Notes

Reaction equation

HRID 1530188 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1>C1(C)C=CC=CC=1>[C:1]([O:9][CH2:1][CH2:2][CH2:7][CH3:6])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

3

Reactant 1

HCID 938Nicotinic Acid

Product 1

HCID 813533-Pyridinecarboxylic acid, butyl esterYield 192.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
116 °C

Procedure

N-butanol (133.2 g, 1.8 mol), nicotinic acid (73.8 g, 0.6 mol) and toluene (45.0 g) were charged to a 450 mL pressure reactor kettle equipped with mechanical stir, a pressure take-out trap, and a thermocouple. The reactor was sparged with nitrogen and heated to 116° C., sealed, then heated to 220° C. and held for 6 hours. The mixture was then removed from the reaction kettle and volatiles removed under vacuum on a rotary evaporator at 60° C. The product was then filtered through celite on a Buchner funnel. 103.4 g product was obtained.

Workup

  1. customequipped with mechanical stir
  2. customThe reactor was sparged with nitrogen
  3. customsealed
  4. temperatureheated to 220° C.
  5. customThe mixture was then removed from the reaction kettle and volatiles
  6. customremoved under vacuum on a rotary evaporator at 60° C
  7. filtrationThe product was then filtered through celite on a Buchner funnel

Sources & evidence

ORD record
ord-f8aee6ffb23048fca4c8c8930562abb7
Source dataset
uspto-grants-2015_07
Patent number
US09090847B2

Reaction notes

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