1-Butanol → 3-Pyridinecarboxylic acid, butyl ester

HRID 1530182Notes

Reaction equation

HRID 1530182 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH3:4].[C:6]([OH:14])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[N:9][CH:8]=1>C1(C)C=CC=CC=1>[C:6]([O:14][CH2:1][CH2:2][CH2:3][CH3:4])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[N:9][CH:8]=1

Participants

4

Reactant 2

HCID 2631-ButanolHCID 938Nicotinic Acid

Product 1

HCID 813533-Pyridinecarboxylic acid, butyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
116 °C

Procedure

n-Butanol (177.6 g, 2.4 mol), nicotinic Acid (98.4 g, 0.8 mol) and toluene (45.0 g) were charged to a 450 ml pressure reactor kettle and 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 200° 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 purified by combining it with 50.0 g toluene and 60.1 g 4.4% NaOH solution in a 500 mL separatory funnel. The organic layer was then separated, dried over 5 g MgSO4 and solvents removed under vacuum on a rotary evaporator at 60° C. to yield the desired product.

Workup

  1. customequipped with mechanical stir
  2. customThe reactor was sparged with nitrogen
  3. customsealed
  4. temperatureheated to 200° 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. customThe product was then purified
  8. customThe organic layer was then separated
  9. dry with materialdried over 5 g MgSO4 and solvents
  10. customremoved under vacuum on a rotary evaporator at 60° C.

Sources & evidence

ORD record
ord-fa7b7cfa584244deb1d82159edc9849f
Source dataset
uspto-grants-2015_07
Patent number
US09090847B2

Reaction notes

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