Trifluoroacetic acid → [2-(3,4-Dihydro-1H-isoquinolin-2-yl)ethyl]-(7-nitro-3,4-dihydro-2H-naphthalen-1-ylidene)amine

Participants

Role	Name	HCID	Charge
Reactant	Trifluoroacetic acid	HCID 6422	—
Reactant	7-Nitro-1-tetralone	HCID 38445	—
Reactant	2-(1,2,3,4-Tetrahydroisoquinolin-2-yl)ethan-1-amine	HCID 40742	—
Solvent	Toluene	HCID 1140	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	[2-(3,4-Dihydro-1H-isoquinolin-2-yl)ethyl]-(7-nitro-3,4-dihydro-2H-naphthalen-1-ylidene)amine	HCID 58958206	94%

Reaction Conditions

Temperature	130 °C

Reaction Steps

To a solution of 36 (964 mg, 5.48 mmol) and 7-nitro-3,4-dihydro-2H-naphthalen-1-one (95) (1.05 g, 5.48 mmol) in toluene (30 mL) was added a catalytic amount of TFA. The reaction was heated at 130° C. overnight before it was allowed to cool to room temperature and diluted with EtOAc (100 mL). The organic solution was sequentially washed with saturated NaHCO3 (aq. 100 mL), brine (100 mL), dried over Na2SO4, and concentrated to give 96 as a brown oil (1.8 g, 94%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07265122B2
Source dataset	uspto-grants-2007_09
ORD ID	ord-875f97cde2c04a11a6c7244706e0814f
Source note	uspto-grants-2007_09