Acetic Acid → Methyl Nicotinate

HRID 1831848Notes

Reaction equation

HRID 1831848 reaction equation
[C:1]([O:9][CH3:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.O.[C:12](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])[CH3:12].[C:1]([O:9][CH3:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 7151Methyl Nicotinate

Product 2

HCID 7151Methyl NicotinateHCID 95893-Acetylpyridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

An electrically heated tubular reactor with an i. d. of 12 mm was filled with 15 ml (≈15 g) of catalyst prepared according to EP-A-0 352 674, example 1. Over a period of 60 h, a mixture of methyl nicotinate (78 g), water (149 g) and acetic acid (523 g) was metered using a precision pump to the reactor operating at 410° C. From the reaction mixture, 30.5 g of 3-acetylpyridine, 8.5 g of pyridine and 9.0 g of methyl nicotinate were obtained. This corresponded to a yield of 45% 3-acetylpyridine at a methyl nicotinate conversion of 88% (selectivity 50%). The selectivity of pyridine formation was 19%.

Workup

  1. customprepared
  2. customoperating at 410° C

Sources & evidence

ORD record
ord-ef4d77720ef249c088ce7cf296f5ef26
Source dataset
uspto-grants-2006_06
Patent number
US07067673B2

Reaction notes

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