Acetic Acid → 3-Acetylpyridine

HRID 1831847Notes

Reaction equation

HRID 1831847 reaction equation
[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.O.[C:15](O)(=O)C>N1C=CC=CC=1>[C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)(=[O:9])[CH3:15].[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

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 813533-Pyridinecarboxylic acid, butyl ester

Product 2

HCID 95893-AcetylpyridineHCID 813533-Pyridinecarboxylic acid, butyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

An electrically heated tubular reactor with an inner diameter (i. d.) of 12 mm was filled with 15 ml (12 g) of catalyst from example 1. Over a period of 12 h, a mixture of 17.9 g butyl nicotinate, 32 g water and 125 g acetic acid was metered using a precision pump to the reactor operating at 410° C. From the reaction mixture, 8.9 g of 3-acetylpyridine, 0.9 g of pyridine and 1.3 g of butyl nicotinate were obtained. This corresponded to a yield of 73% 3-acetylpyridine at a butyl nicotinate conversion of 93% (selectivity 78%). The selectivity of pyridine formation was 11%.

Workup

  1. customoperating at 410° C

Sources & evidence

ORD record
ord-90c3a4fe2ab645ca8563e8c6d5a4d0f2
Source dataset
uspto-grants-2006_06
Patent number
US07067673B2

Reaction notes

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