Reaction #1994248

Reaction equation

8-nitro-2-naphthylquinoline

sodium borohydride

HCl

→

crystalline solid

Yield 135.5%

8-Amino-2-naphthylquinoline

Yield 135.5%

Solvents

methanol

Conditions

Workup

1. 1
   workup.STIRRINGAfter stirring for 2 h
2. 2
   OtherThe solvent is then removed
3. 3
   Washthe resultant residue is washed vigorously with water
4. 4
   Otherrecrystallised from dioxane
5. 5
   FiltrationThe precipitate is filtered
6. 6
   Otherdried in vacuo

Procedure

12.6 g (42 mmol) of 8-nitro-2-naphthylquinoline and 1.99 g of Pd/C (10%) are suspended in 200 ml of methanol. 8.4 g (222 mmol) of sodium borohydride are added in portions with stirring at 0° C. After stirring for 2 h, the clear solution is neutralised using dilute HCl. The solvent is then removed, and the resultant residue is washed vigorously with water and recrystallised from dioxane. The precipitate is filtered and dried in vacuo, giving 9.9 g (56.9 mmol) of crystalline solid. The overall yield is 88%.

Source