Sodium Hydroxide → 2-Chloro-5-methylpyridin-4-amine

Participants

Role	Name	HCID	Charge
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	2-Chloro-5-methyl-4-nitropyridine N-oxide	HCID 12318010	—
Catalyst	Iron	HCID 23925	—
Solvent	Acetic Acid	HCID 176	—
Product	2-Chloro-5-methylpyridin-4-amine	HCID 12643706	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

Iron (1.0 g) was added to a solution of 10 (500 mg, 2.6 mmol) in glacial acetic acid (10 mL). The reaction mixture was then heated at 100° C. for 20 minutes. The suspension was poured on aqueous NaOH 1M and extracted with ethyl acetate. After drying over Na2SO4, the solvent was then evaporated and 11 was isolated as a colorless solid (370 mg, 2.6 mmol, HPLC Rt 1.3 min, FIA ES+ 143.0).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07345054B2
Source dataset	uspto-grants-2008_03
ORD ID	ord-e36af1263d424eb897e5e607beff04d6
Source note	uspto-grants-2008_03