Trimethylsilyldiazomethane → Methyl 5,6-Dichloronicotinate

HRID 1820968Notes

Reaction equation

[Cl:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:12][Si](C=[N+]=[N-])(C)C>>[Cl:1][C:2]1[C:3]([Cl:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([O:9][CH3:12])=[O:8]

Participants

Reactant 2

HCID 167693Trimethylsilyldiazomethane

HCID 2479875,6-Dichloronicotinic acid

Product 1

HCID 2782166Methyl 5,6-DichloronicotinateYield 80.2%

Procedure

To a solution of 2.15 g (11.2 mmol) of 5,6-dichloronicotinic acid in 10 mL of v:v 1:1 CHCl2/CH3OH at rt was added dropwise 8.4 mL (16.8 mmol) of (trimethylsilyl)diazomethane (2.0 M in hexanes). The mixture was stirred at rt for 30 min and then concentrated. Chromatography on a Biotage 40M cartridge using 1:19 v/v EtOAc/hexanes as the eluant gave 1.85 g of the title compound: 1H NMR (500 MHz, CDCl3) δ 3.98 (s, 3H), 8.35 (d, J=1.8, 1H), 8.88 (d, J=1.8, 1H).

Workup

concentrationconcentrated

Sources & evidence

ORD record: ord-e1df5c03cdcd492bbd7e438fc34b8483
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605171B2

Reaction notes

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