Isoamyl Nitrite → HCID 20093457, compound

Participants

Reaction Steps

To a stirred solution of 5-butylamino-1,3dimethylpyrazole (4.0 g, 23.9 mmol) in EtOH (100 mL) there was added dropwise, under nitrogen, isoamyl nitrite (35 mL) and the mixture was stirred at room temperature for 3 hours. The progress of the reaction was monitored by tlc (SiO2, developed with EtOAc/hexanes [3:2]) and when no starting material remained, the solution was evaporated to dryness. This mixture was purified by chromatography on a SiO2 column (400 mL) developed with EtOAc/hexanes (40:60). The faster components were eluted first (one of which is the isomeric N-nitroso derivative which can be isomerized with acid to yield additional product) followed by the Step C compound (3.23 g, 69%) as reddish crystals. 1H NMR (200 MHz, CDCl3)δ 3.77 (s, 3H), 3.47 (d of t, 2H), 2.61 (s, 3H), 1.53-1.70 (m, 2H), 1.37-1.52 (m, 2H), 0.96 (t, 3H, J=9 Hz). M.p 49°-101° C. Anal. Calcd for C4H16N4O; C, 55.08; H, 8.22; N, 28.55; Found: C, 55.11; H, 8.16; N, 28.23.

Provenance & Evidence