Acetic Acid → 3-Pyridinecarbonitrile, 1,2-dihydro-6-methyl-2-oxo-

HRID 1658528Notes

Reaction equation

HRID 1658528 reaction equation
CO[CH:3]=[CH:4][C:5](=O)[CH3:6].[C:8]([CH2:10][C:11]([NH2:13])=[O:12])#[N:9].C(O)(=O)C.N1CCCCC1>O.COCCO>[C:8]([C:10]1[C:11](=[O:12])[NH:13][C:4]([CH3:3])=[CH:5][CH:6]=1)#[N:9]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7898CyanoacetamideHCID 8082PiperidineHCID 942973-Buten-2-one, 4-methoxy-

Product 1

HCID 779193-Pyridinecarbonitrile, 1,2-dihydro-6-methyl-2-oxo-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 150 g (1.5 m) of 4-methoxy-3-buten-2-one, 126 g (1.5 m) of α-cyanoacetamide, and catalyst (6 cc of glacial acetic acid in 15 cc of water made basic with piperidine) in 750 cc of methyl cellosolve is refluxed and stirred for 3 hours. The solution which forms is concentrated in vacuo and the residue semi-solid is boiled in an excess of isopropanol and filtered hot. The first crop is dried to afford a 94.5 g (47%) yield of 3-cyano-6-methyl-2-pyridone, m.p. 245-246 dec. A mixture of 72 g (.537 m) of this product and 600 cc of 12N hydrochloric acid is refluxed and stirred for 6 hours. The solution is allowed to stand at room temperature for 3 days and is concentrated in vacuo. The residue solid is recrystallized with ethanol to afford a 43 g (52.5%) yield of 1H, 3-carboxy-6 -methylpyridin-2-one, m.p. 226°.

Workup

  1. temperatureis refluxed
  2. concentrationThe solution which forms is concentrated in vacuo
  3. filtrationfiltered hot
  4. customThe first crop is dried

Sources & evidence

ORD record
ord-f4fac2ab32cc47dc9188e2c65b606bbc
Source dataset
uspto-grants-1976_06
Patent number
US03965107

Reaction notes

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