Hydrochloric Acid → 6-Cyclopropylpyridin-2-amine

Participants

Role	Name	HCID	Charge
Reactant	Hydrochloric Acid	HCID 313	—
Reactant	N-(6-Cyclopropyl-pyridin-2-yl)-2,2-dimethyl-propionamide	HCID 60019882	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	6-Cyclopropylpyridin-2-amine	HCID 45787863	77.5%

Reaction Conditions

Temperature	90 °C

Reaction Steps

To a solution of N-(6-cyclopropylpyridin-2-yl)pivalamide (4.25 gm, 19.49 mmol) in dioxane (34 ml) was added 9N HCl (34 ml). The mixture was stirred for 18 hours at 90° C. After cooling to 25° C., the pH of the reaction was adjusted with to achieve pH-9. The solution was diluted with ethyl acetate (200 ml) quantity and washed with saturated sodium bicarbonate. Next, the organic portion was dried over sodium sulfate and concentrated to get 2 gm (77.5% yield) clear oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-6a034a10a9ee499ab6e3d2523d91d625
Source note	uspto-grants-2016_05