tert-butyl 7-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate → tert-butyl 7-[amino(hydroxyimino)methyl]-3,4-dihydroisoquinoline-2(1H)-carboxylate

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Reaction Steps

The title compound was prepared following procedure described for Intermediate 1, step 2, but starting from tert-butyl 7-cyano-3,4-dihydroisoquinoline-2(1H)-carboxylate obtained in step 1 (1.50 g; 5.81 mmol). The solvent was evaporated in vacuo and further freeze dried to give the title compound as an off-white solid (1.35 g, 80%). 1H NMR (DMSO-d6) δ 9.54 (s, 1H), 7.46 (m, 2H), 7.14 (d, J=8 Hz, 1H), 5.74 (bs, 2H), 4.49 (s, 2H), 3.54 (t, J=5.9 Hz, 2H), 2.76 (t, J=5.9 Hz, 2H), 1.49 (s, 9H). HPLC (Method A), Rt 2.40 min (Purity: 99.4%). LC/MS (Method B): 292.2 (M+H)+.

Provenance & Evidence