Methanol → 2-Methoxy-3-nitro-5-ethyl-6-methylpyridine

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	Sodium	HCID 5360545	—
Reactant	2-Chloro-5-ethyl-6-methyl-3-nitropyridine	HCID 10375547	—
Solvent	Diethyl Ether	HCID 3283	—
Product	2-Methoxy-3-nitro-5-ethyl-6-methylpyridine	HCID 10465270	80%

Reaction Conditions

Temperature	50 °C

Reaction Steps

Sodium metal (100 mg, 4.3 mmol) was dissolved in methanol (5 mL) under a nitrogen atmosphere. A solution of 2-chloro-3-nitro-5-ethyl-6-methylpyridine (677 mg, 3.37 mmol) in methanol (5 mL) was added dropwise. The reaction was warmed at 50° C. for four hours. The reaction was cooled, diluted with diethyl ether, the ether layer washed with water, dried (Na2SO4), filtered through a pad of charcoal and evaporated to yield 535 mg (80%) of product.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05308854
Source dataset	uspto-grants-1994_05
ORD ID	ord-5cc1a9aad7fe434096b3070cd9bc941f
Source note	uspto-grants-1994_05