Methanol → Methyl 6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 870807Notes

Reaction equation

HRID 870807 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][N:7]=1.[CH3:15]O>>[CH3:15][O:11][C:10]([C:9]1[CH:13]=[CH:14][C:6](=[O:5])[NH:7][CH:8]=1)=[O:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178418479HCID 178418479, compound

Product 1

HCID 416343Methyl 6-oxo-1,6-dihydropyridine-3-carboxylateYield 68%

Procedure

Thionyl chloride (6.3 mL, 86.33 mmol) was added dropwise to a solution of 6-hydroxynicotinic acid (10.0 g, 71.94 mmol) in methanol at 0° C. The mixture was heated to reflux for 6 hours, the solvent was removed and standard extractive work up provided the title compound as a brown solid (7.5 g, 68%). m.p. 166-172° C.; 1H NMR (400 MHz, DMSO-d6) δ 3.77 (s, 3H), 6.37 (d, J=9.3 Hz, 1H), 7.79 (dd, J=2.7, 9.5 Hz, 1H), 8.04 (d, J=2.4 Hz, 1H); IR (KBr) υ 3050, 2965, 1712, 1651, 1433, 1300, 1106 cm−1; MS 154 (M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 hours
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-bacbe2abc7ab4815a7c675b375c6c77d
Source dataset
uspto-grants-2015_03
Patent number
US08969576B2

Reaction notes

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