Ammonia → 2-Chloro-6-methoxyquinolin-4-amine

Participants

Role	Name	HCID	Charge
Reactant	Ammonia	HCID 222	—
Reactant	Methanol	HCID 887	—
Reactant	2,4-Dichloro-6-methoxyquinoline	HCID 948356	—
Product	2-Chloro-6-methoxyquinolin-4-amine	HCID 86689939	55%

Reaction Conditions

Temperature	150 °C

Reaction Steps

A suspension of 2,4-dichloro-6-methoxyquinoline (5.00 g, 22.0 mmol) in NH3 (g)/MeOH (saturated, 40 mL) was heated to 150° C. for 16 hours in a sealed tube. The solvent was removed and the residue was diluted with MeOH (20 mL). The mixture was filtered off and the filtrate was concentrated to give the crude product. Purification by column chromatography on silica gel (PE/EtOAc=2/1) gave product (7.50 g, yield: 55%) as a solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09433618B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-407dae5f4068404986288ea6c7337ca7
Source note	uspto-grants-2016_09