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A solution of ethyl 6-chloro-4-(phenylamino)nicotinate (19 g, 89 mmol) in anhydrous THF (40 mL) was added dropwise to a 0° C. suspension of LiAlH4 (8.5 g, 223 mmol) in anhydrous THF (80 mL). After complete addition, the reaction mixture was stirred at RT for 3 h. The mixture was quenched by the addition of 10% aq NaOH (8.5 mL) and water (8.5 mL). The solids were removed by filtration and the organic phase was concentrated in vacuo to provide (6-chloro-4-(phenylamino)pyridin-3-yl)methanol (12 g, 80% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.09 (s, 1 H), 8.08 (s, 1 H), 7.39-7.10 (m, 5 H), 6.73 (s, 1 H), 5.37 (s, 1 H), 4.52 (s, 2 H).

1. additionAfter complete addition
2. customThe mixture was quenched by the addition of 10% aq NaOH (8.5 mL) and water (8.5 mL)
3. customThe solids were removed by filtration
4. concentrationthe organic phase was concentrated in vacuo