Methoxyacetyl chloride → Methyl 6-chloro-5-methoxyacetamidonicotinate

HRID 50334Notes

Reaction equation

HRID 50334 reaction equation
[NH2:1][C:2]1[C:3]([Cl:12])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH3:13][O:14][CH2:15][C:16](Cl)=[O:17]>ClC1C=CC=CC=1>[Cl:12][C:3]1[C:2]([NH:1][C:16](=[O:17])[CH2:15][O:14][CH3:13])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 18412438Methyl 5-amino-6-chloropyridine-3-carboxylate

Product 1

HCID 18412377Methyl 6-chloro-5-methoxyacetamidonicotinate

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of 0.75 g (4.02 mmol) of methyl 5-amino-6-chloronicotinate and 0.43 g=0.35 mL (4.5 mmol) of methoxyacetylchloride in 20 mL of chlorobenzene was stirred for one hour at 110° C. After the solvent had been removed in vacuo, the crude product obtained was purified by flash chromatography (silica gel; methylene chloride/ethanol=100:1), evaporated down again in vacuo and then digested with petroleum ether. Yield: 0.55 g (53% of theory) light yellow amorphous solid; Rf value: 0.33 (silica gel; ethyl acetate/petroleum ether=1:4).

Workup

  1. customAfter the solvent had been removed in vacuo

Sources & evidence

ORD record
ord-92eaf636d47c4163a84089a85fb8eefe
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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