反应详情

温度

0 °C

To a suspension of 2-tert-Butyl-5-nitro-phenylamine (4.04 g, 20.80 mmol) in CH2Cl2 (20 mL) at 0° C. was added 1.1 equiv of Methyl chlorooxoacetate (2.10 mL, 22.88 mmol) and followed by dropwise addition of 1.1 equiv of Et3N (3.19 mL, 22.88 mmol). After stirring at 0° C. and allowing to warm up to room temperature over 4 hrs, the reaction mixture was treated with water (20 mL), stirred for 10 min and then partitioned between EtOAc/water. The organic phase was washed with 0.5N HCl (2×25 mL), and saturated NaCl solution (50 mL), dried over Na2SO4 and evaporated to dryness. The residue was purified by flask column chromatography on silica gel eluting with EtOAc/Hexane (5–25%) to give the title compound (3.25 g, 56%) as light yellow crystals. TLC (30% EtOAc/Hexane) Rf=0.39; 1HNMR (CDCl3) δ 9.36 (br.s, 1H), 8.97 (d, J=2.4 Hz, 1H), 8.02 (dd, J=9.0, 2.4 Hz, 1H), 7.60 (d, J=9.0 Hz, 1H), 4.03 (s, 3H), 1.52 (s, 9H).

1. temperatureto warm up to room temperature over 4 hrs
2. stirringstirred for 10 min
3. custompartitioned between EtOAc/water
4. washThe organic phase was washed with 0.5N HCl (2×25 mL), and saturated NaCl solution (50 mL)
5. dry with materialdried over Na2SO4
6. customevaporated to dryness
7. customThe residue was purified by flask column chromatography on silica gel eluting with EtOAc/Hexane (5–25%)