Methyl 6-amino-5-(hydroxymethyl)-2-methyl-4-(p-tolyl)nicotinate → Methyl 6-amino-5-formyl-2-methyl-4-(p-tolyl)nicotinate

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Reaction Steps

A suspension of methyl 6-amino-5-(hydroxymethyl)-2-methyl-4-(p-tolyl)nicotinate (3.14 g, 10.97 mmol) in dichloromethane (DCM) (100 ml) was treated with PCC (2.84 g, 13.16 mmol) and stirred at rt for 1 day. The mixture was filtered through Celite™, washed with DCM, and concentrated. Purification with column chromatography (0-100% EtOAc/Hexane) afforded methyl 6-amino-5-formyl-2-methyl-4-(p-tolyl)nicotinate (2.45 g, 8.62 mmol, 79% yield) as yellow solid: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.60 (s, 1 H), 7.26-7.21 (m, 2 H), 7.19-7.13 (m, 2 H), 3.48 (s, 3 H), 2.49 (s, 3 H), 2.41 (s, 3 H); LCMS (m/z) ES+=285 (M+1).

Provenance & Evidence