反应详情

A solution of 4-nitrophenylacetic acid (2.81 mmol) in dry dichloromethane (10 mL) was treated with a 2N solution of oxalyl chloride (3.0 mL) and DMF (0.02 mL) via syringe, and the reaction stirred at ambient temperature for 1 h. The reaction was concentrated to dryness in vacuo and the crude product was dissolved in dry dichloro-methane (20 mL), treated with anhydrous hydrazine (11.1 mmol) via syringe, and stirred at ambient temperature for 18 h. The resulting suspension was filtered, solids rinsed with dichloromethane, dissolved in MeOH/CH2Cl2, filtered, and filtrate concentrated in vacuo giving the title compound as an orange solid. 1H NMR (DMSO-d6) δ 8.17 (2H, d, J=8.8 Hz,), 7.54 (2H, d, J=8.8 Hz), 3.54 (2H, s).

1. concentrationThe reaction was concentrated to dryness in vacuo
2. dissolutionthe crude product was dissolved in dry dichloro-methane (20 mL)
3. stirringstirred at ambient temperature for 18 h
4. filtrationThe resulting suspension was filtered
5. washsolids rinsed with dichloromethane
6. dissolutiondissolved in MeOH/CH2Cl2
7. filtrationfiltered
8. concentrationfiltrate concentrated in vacuo