Isoquinolin-3-Amine → 5,6,7,8-Tetrahydroisoquinolin-3-amine

Using the method of Example 63, Step A, 75 mg of 3-aminoisoquinoline (7.73 mmoles) and 8.7 mg platinum oxide in 2 mL of trifluoroacetic acid was shaken under 40 psi of hydrogen for 3 h. The mixture was filtered and catalyst was washed with ethyl acetate. After concentrating the filtrate, the residue was dissolved in 10 mL of ethyl acetate and washed with 5 mL of saturated aquous sodium bicarbonate. The organic solution was dried (sodium sulfate), decanted, and concentrated to give a yellow syrup. Flash coumn chromatography on 19 g of silica gel, eluting with 600 mL of 50% ethyl acetate/hexane gave 26.5 mg (34% yield) of 3-amino-5,6,7,8-tetrahydroisoquinoline as a pale yellow solid.

1. filtrationThe mixture was filtered
2. washcatalyst was washed with ethyl acetate
3. concentrationAfter concentrating the filtrate
4. dissolutionthe residue was dissolved in 10 mL of ethyl acetate
5. washwashed with 5 mL of saturated aquous sodium bicarbonate
6. dry with materialThe organic solution was dried (sodium sulfate)
7. customdecanted
8. concentrationconcentrated
9. customto give a yellow syrup
10. washFlash coumn chromatography on 19 g of silica gel, eluting with 600 mL of 50% ethyl acetate/hexane

ORD record

ord-590e9480a04b43cd8fc401785bc627d0

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05972975