Sodium borohydride → 2-(Hydroxymethyl)-6-nitrobenzonitrile

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Reaction Steps

Sodium borohydride (92.0 mg, 2.43 mmol) was added to a solution of 2-formyl-6-nitrobenzonitrile (Example 207e) (0.86 g, 4.88 mmol) in MeOH (38 mL) and THF (38 mL) at −8° C., and was stirred at that temperature for no more than 30 min. The reaction was quenched with HCl (6 M, 4.88 mL), followed by addition of water (50 mL), and brine (50 mL). The mixture was extracted with EtOAc, the combined extract was dried over MgSO4, filtered and concentrated. The crude product was purified by chromatography on silica using the solvent gradient CH2Cl2→CH2Cl2/MeOH (8:2) to give the title compound in amount of 0.32 g, (37%), which was used immediately in the next step. 1H NMR (400 MHz, DMSO-d6) δ 4.77 (d, J=5.6 Hz, 2H), 5.87 (t, J=5.6 Hz, 1H), 7.97 (t, J=8.0 Hz, 1H), 8.07 (dd, J=0.4, 8.0 Hz, 1H), 8.28 (dd, J=0.8, 8.0 Hz, 1H).

Provenance & Evidence