Phosphorus oxychloride → Methyl 6-chloro-3-methylpyridine-2-carboxylate

HRID 2201579Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][N+:6]=1[O-])=[O:4].O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:7]1[N:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[C:10]([CH3:11])=[CH:9][CH:8]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 727140222-(Methoxycarbonyl)-3-methylpyridine 1-oxide

Product 1

HCID 45489870Methyl 6-chloro-3-methylpyridine-2-carboxylateYield 37%

Procedure

A solution of 2-(methoxycarbonyl)-3-methylpyridine 1-oxide (2 g, 6.0 mmol) in POCl3(5 mL) was stirred at 100° C. for 3 hours. After being concentrated, the residue was purified by column chromatography (PE:EtOAc=1:1) to give the product of methyl 6-chloro-3-methylpicolinate (380 mg, yield: 37%). 1H-NMR (CDCl3, 400 MHz) δ 7.59 (d, J=8.0 Hz, 1H), 7.38 (d, J=8.0 Hz, 1H), 3.96 (s, 3H), 2.56 (s, 3H). MS (M+H)+: 186/188.

Workup

concentrationAfter being concentrated
customthe residue was purified by column chromatography (PE:EtOAc=1:1)

Sources & evidence

ORD record: ord-6f56eae3622f47c48bc47ed4afa9b438
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09364482B2

Reaction notes

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