Reacción #969880

Ecuación de reacción

(2-formylphenyl)boronic acid pinacol ester

isonicotinic acid hydrazide

→

Isonicotinic acid [2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzylidene]-hydrazide

Rendimiento 67.0%

Disolventes

sodium acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe white insoluble product was collected via vacuum filtration
2. 2
   Lavadowashed with water
3. 3
   Otrodried in vacuo
4. 4
   Otroto give an off-white powder in 67% yield
5. 5
   OtroRecrystallization
6. 6
   Otroby slow evaporation of CH2Cl2 or vapor diffusion of CH2Cl2 and hexanes afforded translucent plates suitable for X-ray diffraction

Procedimiento

A portion of (2-formylphenyl)boronic acid pinacol ester (1 mmol, 0.232 g) was added to a nearly saturated solution of isonicotinic acid hydrazide (1 mmol, 0.137 g) in 0.1 M pH 4.5 sodium acetate buffer. The reaction mixture was stirred over an oil bath at 100° C. in for 4 min. The white insoluble product was collected via vacuum filtration, washed with water, and dried in vacuo to give an off-white powder in 67% yield. Recrystallization by slow evaporation of CH2Cl2 or vapor diffusion of CH2Cl2 and hexanes afforded translucent plates suitable for X-ray diffraction. 1H NMR (DMSO): δ 1.341 (12H, s), 7.447 (2H, td, J=1.20, J=6.47), 7.565 (1H, t, J=7.07), 7.736 (1H, d, J=6.72), 7.818 (2H, dd, J=1.47, J=4.49), 8.029 (1H, d, J=7.68), 8.791 (2H, d, J=5.8), 8.963 (1H, s), 12.20 (1H, s); 13C NMR (DMSO): δ 62.07, 121.45, 138.27, 159.21, 163.11, 166.70, 168.59, 173.04, 176.79, 186.85, 187.74, 187.89; MS (ESI): m/z 352.3 (M+H+), 374.3 (M+Na+), 350.1 (M−H+); IR (neat, cm−1): 3179, 3059, 2974, 1643, 1550, 1479, 1346, 1292, 1141. 1056; UV-vis (MeOH) nm (M−1 cm−1): 208 (20,320), 302 (19,530).

Fuente