Methylamine → N-methyl-1-benzofuran-6-amine

Participants

Role	Name	HCID	Charge
Reactant	Methylamine	HCID 6329	—
Reactant	Potassium Acetate	HCID 517044	—
Reactant	6-Bromo-1-benzofuran	HCID 15158722	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ammonium Hydroxide	HCID 14923	—
Product	N-methyl-1-benzofuran-6-amine	HCID 118597876	33.3%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 6-bromo-1-benzofuran (1.0 g, 5.1 mmol), methylamine (2N, 25 mL, 50 mmol), CuI (1.16 g, 6.1 mmol) and KOAc (1.25 g, 12.7 mmol) in DMF (10 mL) was stirred overnight at 100° C. under nitrogen in a sealed tube. The mixture was cooled to r.t., diluted with aqueous ammonium hydroxide, and extracted with EtOAc. The organic layer was concentrated, and the residue was purified by silica gel chromatography to give 250 mg (33%) of the title compound as a yellow oil. [M+H] Calc'd for C9H9NO, 148. Found, 148.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09447046B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-d3ade9fe2c204cc685f51d862a99956b
Source note	uspto-grants-2016_09