Water → 5-(Oxazolo[5,4-c]pyridin-2-yl)thiophen-2-amine

Participants

Reaction Steps

A mixture of 2-(5-nitrothiophen-2-yl)oxazolo[5,4-c]pyridine (170 mg, 0.69 mmol), NH4Cl (199 mg, 3.73 mmol), iron powder (328 mg, 5.87 mmol), H2O (10 mL) and methanol (40 mL) was heated to reflux for 6 hrs under N2. The mixture was concentrated in vacuo followed by addition of 100 mL of water and left overnight at 4° C. The precipitate was collected by filtration and dried to give 5-(oxazolo[5,4-c]pyridin-2-yl)thiophen-2-amine as a brown solid (52 mg, yield 35%). 1HNMR (400 MHz, DMSO-d6) δ: 8.84 (1H, s); 8.40 (1H, d, J=5.2); 7.64 (1H, d, J=4); 7.57 (1H, d, J=5.2), 7.06 (2H, s), 1.09 (1H, d, J=4.4).

Provenance & Evidence