3-Methylpyridine → Nicotinic Acid

HRID 1181665Notes

Reaction equation

HRID 1181665 reaction equation
[OH:1]N1C(=O)C2=CC=CC=C2C1=O.[CH:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1.N1C=CC=C(C)C=1>C(O)(=O)C.C([O-])(=O)C.[Co+2].C([O-])(=O)C.C([O-])(=O)C.[Mn+2].C([O-])(=O)C>[C:13]([OH:1])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][CH:15]=1

Participants

7

Reactant 3

HCID 79703-MethylpyridineHCID 103713-PyridinecarboxaldehydeHCID 10665N-Hydroxyphthalimide

Product 1

HCID 938Nicotinic Acid

Reagents, catalysts & solvents 3

HCID 6277Cobalt diacetateCatalystHCID 12525Manganous AcetateCatalystHCID 176Acetic AcidSolvent

Procedure

In the presence of an oxidation catalyst (N-hydroxyphthalimide (NHPI)) and a metal catalyst (cobalt acetate and manganese acetate) with nicotinaldehyde as a co-oxidizing agent, β-picoline was oxidized in acetic acid solvent at 140° C. and 2 MPa with air to produce nicotinic acid. From the reaction mixture, acetic acid was removed, to the condensate was added 2-ethylhexanol. The mixture was cooling-crystallized to 25° C. at atmospheric pressure and filtrated, and the residue washed with methanol and filtrated to separate nicotinic acid. The components in the mixture obtained by combining the filtrate and washing liquid were analyzed, and as a result, 9.4 g of nicotinic acid, 160 g of 2-ethylhexanol, 32 g of acetic acid, 63 g of β-picoline, 150 g of methanol, 0.5 g of N-hydroxyphthalimide (NHPI), 10 g of phthalic acid (PA), 8 g of phthalimide (PI), 2.5 g of phthalic anhydride (APA), 1.1 g of total cobalt, 1.1 g of total manganese were contained.

Sources & evidence

ORD record
ord-467fc4bc188343aaafb67c21812417fe
Source dataset
uspto-grants-2007_10
Patent number
US07285684B2

Reaction notes

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