Ethyl 2-chloroacetoacetate → HCID 75076919, compound

Participants

Reaction Conditions

Reaction Steps

4-Trifluoromethoxybenzenediazonium tetrafluoroborate (63) (4.33 g, 15.7 mmol) was added to a solution of ethyl 2-chloroacetoacetate (64) (2.35 g, 14.3 mmol) in pyridine (6 mL) and water (6 mL) at −5° C. The mixture was stirred at −5° C. for 0.5 h and the precipitate was filtered and washed with ice cold water. Recrystallisation from EtOH/water gave ethyl 2-chloro{[4-(trifluoromethoxy)phenyl]hydrazono}ethanoate (65) (3.977 g, 82%) as pale orange needles: mp 128-130° C.; 1H NMR [(CD3)2SO] δ 10.68 (s, 1H), 7.43 (d, J=9.2 Hz, 2H), 7.34 (d, J=9.2 Hz, 2H), 4.30 (t, J=7.1 Hz, 2H), 1.30 (q, J=7.1 Hz, 3H). APCI MS m/z 309, 311 [M−H]−.

Provenance & Evidence