1-Butanol → 3-Pyridinecarboxylic acid, butyl ester

HRID 1530181Notes

Reaction equation

HRID 1530181 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH2:10](O)[CH2:11][CH2:12][CH3:13]>CCCCCCC>[C:1]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 2631-ButanolHCID 938Nicotinic Acid2×

Product 1

HCID 813533-Pyridinecarboxylic acid, butyl ester

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
115 °C

Procedure

Nicotinic Acid (24.6 g, 0.2 mol), n-butanol (100.0 g, 1.33 mol) and heptane (20.1 g) were charged to a 500 mL reaction kettle and equipped with mechanical stir, a Dean-Stark trap, and thermocouple. The mixture was stirred at 300 rpm under nitrogen atmosphere and alkylbenzenesulfonic acid (480 mw, 120 g, 0.25 mol) was added dropwise through an addition funnel over 2 hours. The mixture was heated to 115° C. and held for 3 hours. A second portion of Nicotinic Acid (24.6 g, 0.2 mol) was added through a powder funnel and the temperature was increased to 150° C. and vacuum was applied to −29.5 in Hg and held for 1 hour. The distillate was then taken and solvents removed under vacuum on a rotary evaporator to yield the desired product. This process was repeated 2 additional times using the same Alkylbenzenesulfonic acid.

Workup

  1. customequipped with mechanical stir
  2. temperaturethe temperature was increased to 150° C.
  3. waitheld for 1 hour
  4. customsolvents removed under vacuum on a rotary evaporator

Sources & evidence

ORD record
ord-735beb3138e94a05a2b705e019c72c43
Source dataset
uspto-grants-2015_07
Patent number
US09090847B2

Reaction notes

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