Reacción #68941

Ecuación de reacción

HCl

8-Chloroisoquinolin-3-amine

Sodium nitrite

sodium bicarbonate

→

title compound

Rendimiento 45.0%

3,8-Dichloroisoquinoline

Rendimiento 45.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaslowly warming to room temperature over an additional 1 hour
2. 2
   workup.WAITAfter 3 hours
3. 3
   Extracciónextracted into ethyl acetate
4. 4
   ExtracciónThe organic extract
5. 5
   Lavadowas washed with brine
6. 6
   Secadodried (Na2SO4)
7. 7
   Concentraciónconcentrated
8. 8
   LavadoFlash chromatography on silica, eluting with dichloromethane

Procedimiento

8-Chloroisoquinolin-3-amine (724 mg, 4.05 mmol) was suspended in 10 M HCl and cooled to 0° C. Sodium nitrite (336 mg, 4.86 mmol) was added in portions over 10 minutes. The reaction mixture was stirred for 2 hours, slowly warming to room temperature over an additional 1 hour. After 3 hours, the mixture was poured cautiously into saturated sodium bicarbonate solution, and extracted into ethyl acetate. The organic extract was washed with brine, dried (Na2SO4) and concentrated. Flash chromatography on silica, eluting with dichloromethane, gave the title compound as a white solid (362 mg, 1.83 mmol, 45%). 1H NMR (d6-DMSO, 400 MHz) δ 9.40 (br t, 1H, J=0.8 Hz), 8.20 (br s, 1H), 8.00-7.98 (m, 1H), 7.88-7.81 (m, 2H). LCMS (3) Rt=2.49 min; m/z (ESI+) 198 (MH+).

Fuente