Acetone → 5-fluoro-2,3-dihydro-1H-isoindole hydrochloride

Participants

Reaction Steps

A suspension of 20% palladium hydroxide on carbon (4.0 g) and N-benzyl-5-fluoroisoindoline (D7) (44.6 g) in ethanol (475 ml) and conc. hydrochloric acid (d=1.18, 25 ml) was stirred with hydrogen at 50 psi for 18 h at 45° C. The mixture was cooled to ambient temperature and filtered to remove the catalyst. The filtrate was evaporated in vacuo to give a solid which was stirred with acetone (300 ml) for 0.5 h and filtered to give the title compound (D8) as a solid (29.3 g). 1H NMR δ (D6-DMSO): 10.0 (2H, br, s), 7.41-7.46 (1H, m), 7.15-7.29 (2H, m), 4.49 (2H, s), 4.46 (2H, s).

Provenance & Evidence