HCID 67291098, compound → HCID 67291611, compound

Participants

Reaction Steps

To a suspension of 4,4,6-trimethyl-2-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline (12.3 g, 40 mmol) in saturated aqueous ammonium chloride and ethanol (100 mL) was added powder iron (9.3 g, 160 mmol) at room temperature. After addition, the resulting mixture was stirred at reflux under nitrogen for 3 h. The reaction mixture was cooled to room temperature; and filtered through a pad of celite. The solvent of ethanol in filtrate was removed under reduced pressure and the water phase was extracted with ethyl acetate. The combined organic phase was dried, concentrated to give 2-(4,4,6-trimethyl-1,2,3,4-tetrahydroquinolin-2-yl)aniline (9.7 g). The product was used in the next step without further purification. LC/MS m/e obsd. (ESI+) [(M+H)+] 267.1.

Provenance & Evidence