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

To a solution of step-a product (30 g, 0.118 mol) in acetonitrile (240 ml, 8 times), cesium carbonate (71.7 g, 0.22 mol, 1.9 eq) was added and stirred for some time. Ethyl iodide (19.8 g (10.19 ml), 0.12 mol, 1.1 eq) was added and the overall reaction mixture was stirred for 1 hr at rt. Progress of the reaction was monitored by TLC (10% ethyl acetate/hexane, Rf˜0.6). On completion of the reaction, filtered the contents, washed with acetonitrile (2×50 ml) and distilled off the solvent. Residue obtained was diluted with ethyl acetate (200 ml) and washed with water 92×100 ml). Dried the contents over sodium sulfate and distilled off the solvent completely. The crude obtained was taken in diisopropyl ether (100 ml), stirred for 10-15 min and filtered. Solid obtained was washed with diisopropyl ether again and dried to yield the required product as an off white solid (23 g, 69% yield).

1. stirringthe overall reaction mixture was stirred for 1 hr at rt
2. customOn completion of the reaction
3. filtrationfiltered the contents
4. washwashed with acetonitrile (2×50 ml)
5. distillationdistilled off the solvent
6. customResidue obtained
7. washwashed with water 92×100 ml)
8. dry with materialDried the contents over sodium sulfate
9. distillationdistilled off the solvent completely
10. customThe crude obtained
11. stirringstirred for 10-15 min
12. filtrationfiltered
13. customSolid obtained
14. washwas washed with diisopropyl ether again
15. customdried

ORD record

ord-da385b2febdd44d498c34781cce7999e

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08334315B2