Hydrochloric Acid → 6-Chloro-2-methoxy-4-methylpyridine-3-carboxylic acid

HRID 922013Notes

Reaction equation

[H-].[Na+].[CH3:3][OH:4].Cl[C:6]1[C:11]([C:12]([OH:14])=[O:13])=[C:10]([CH3:15])[CH:9]=[C:8]([Cl:16])[N:7]=1.Cl>C1COCC1>[Cl:16][C:8]1[N:7]=[C:6]([O:4][CH3:3])[C:11]([C:12]([OH:14])=[O:13])=[C:10]([CH3:15])[CH:9]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of 9.3 g (231 mmol, 60% w/w in mineral oil) NaH in THF (200 ml) was added a solution of 3.8 ml (93 mmol) Methanol in THF (200 ml) while the temperature was kept at 10-20° C. Subsequently a solution of 20.0 g (97 mmol) of 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid in THF (200 ml) was added and the RM was heated to 70° C. for 16 h. After cooling to RT the mixture was acidified with a 2M aq. HCl to pH 3-4 and was then extracted with EtOAc (2×600 ml). The combined organic layers were washed with water and brine, dried over MgSO4 and concentrated in vacuo. The obtained crude 22.6 g 6-chloro-2-methoxy-4-methyl-pyridine-3-carboxylic acid was used in subsequent reactions without further purification.

Workup

customwas kept at 10-20° C
temperatureAfter cooling to RT the mixture
extractionwas then extracted with EtOAc (2×600 ml)
washThe combined organic layers were washed with water and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-927d6f9a1bd14e728e9880c34adcc3ff
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278103B2

Reaction notes

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