Reaction #632029

Reaction equation

hydrazine

6-Chloro-1,4-ethano-8-phenyl-1,2,3,4-tetrahydro-1,5-naphthyridine

hydrazine

HCl

→

6-hydrazino-1,4-ethano-8-phenyl-1,2,3,4-tetrahydro-1,5-naphthyridine

Solvents

ethanol

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was then heated in a screw
2. 2
   Othercap pressure tube at 150° C. until LCMS
3. 3
   Concentrationconcentrated under vacuum
4. 4
   OtherThe residue was partitioned between chloroform and brine
5. 5
   DryingThe organic layer was dried over anhydrous sodium sulfate
6. 6
   Concentrationconcentrated under vacuum

Procedure

6-Chloro-1,4-ethano-8-phenyl-1,2,3,4-tetrahydro-1,5-naphthyridine (1.03 g) was treated with anhydrous ethanol (10 mL), anhydrous hydrazine (Aldrich, 4.0 mL) and concentrated HCl (0.4 mL). The reaction mixture was then heated in a screw cap pressure tube at 150° C. until LCMS showed complete conversion to the hydrazine (approx. 96 h). The reaction mixture was cooled to ambient temperature, then concentrated under vacuum. The residue was partitioned between chloroform and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum to give 6-hydrazino-1,4-ethano-8-phenyl-1,2,3,4-tetrahydro-1,5-naphthyridine as a pale yellow solid (0.68 g).

Source