Water → Nicotinic Acid

HRID 1731863Notes

Reaction equation

HRID 1731863 reaction equation
[OH-:1].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9]CCO)[CH:4]=1.ClCl.[OH2:15]>>[C:9]([OH:15])(=[O:1])[C:5]1[CH:6]=[CH:7][CH:8]=[N:3][CH:4]=1

Participants

5

Reactant 4

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 178613-PyridinepropanolHCID 24526Chlorine2×

Product 1

HCID 938Nicotinic Acid

Procedure

To a reactor is added 25 ml of 50% aqueous NaOH, sufficient water to bring the volume to 50 ml, and 6.9 g (0.05 mol) of 3-(3-pyridinyl)propanol. The solution is brought to 55° C. and 20 g of cupric hydroxide is added. A pH controller is set to maintain the pH above 10 by the incremental addition of 50% aqueous NaOH. After 5 minutes, chlorine is introduced at approximately 1 g/hr. After 48 hours and about 32 g of chlorine have been added, the reaction mixture is assayed for the appearance of product by high performance liquid chromatography. A yield of 5.96 g of nicotinic acid is obtained. This represents a product yield of 97%. The reaction is illustrated as follows: ##STR9##

Workup

  1. customis brought to 55° C.
  2. temperatureto maintain the pH above 10
  3. waitAfter 48 hours

Sources & evidence

ORD record
ord-5ee4f25d0d5c4ecb819dd5708bfca768
Source dataset
uspto-grants-1986_11
Patent number
US04623726

Reaction notes

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