8-Amino-2-naphthalenol → 8-Amino-1,2,3,4-tetrahydronaphthalen-2-ol

Temperature

70 °C

To a stirred solution of 8-amino-2-naphthol (40 g, 0.25 mol) in THF (800 ml, 20 times), Boc anhydride (54.8 g (57.7 ml), 0.25 mol, 1 eq) was added at rt. The overall reaction mass was heated to 70° C. and maintained for 24 hrs at the same temperature. Progress of the reaction was monitored by TLC (20% ethyl acetate/hexane, Rf˜0.6). On completion of the reaction, solvent was distilled off completely and the residue obtained was taken in ethyl acetate (200 ml). Organic layer was washed with saturated sodium carbonate solution (2×200 ml) followed by with water (2×200 ml), dried the contents over sodium sulfate and concentrated under reduced pressure. The crude obtained was taken in diisopropyl ether (150 ml), stirred for 15 min and filtered. Solid obtained was washed with diisopropyl ether again and dried to yield the required product as an off white solid (49 g, 75% yield).

1. temperaturemaintained for 24 hrs at the same temperature
2. customOn completion of the reaction, solvent
3. distillationwas distilled off completely
4. customthe residue obtained
5. washOrganic layer was washed with saturated sodium carbonate solution (2×200 ml)
6. dry with materialdried the contents over sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe crude obtained
9. filtrationfiltered
10. customSolid obtained
11. washwas washed with diisopropyl ether again
12. customdried

ORD record

ord-c4d137a6bd7f491dbe1cc1e6a38f33dd

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08334315B2