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With potassium hydroxide; sodium hydroxide In neat (no solvent)Heating
General procedure: Potassium hydroxide (3.6 g, 64 mmol) and sodium hydroxide (2.4 g, 60 mmol) weremixed and quickly crushed in a porcelain dish. Then the corresponding aldehyde(15 mmol) was added and the mixture was heated on a hot-plate under stirring until thealdehyde melted and additionally 5 minutes. When liquid aldehydes were used, heatingwas continued until temperature reached 140C. After cooling, the crude solid productmixture was added to water (100 mL) and ice (30 g) and acidified with hydrochloric acidto pH 4. The precipitate was collected, dried and recrystallized from ethanol.
Reference：
[1] Organic Preparations and Procedures International, 2017, vol. 49, # 1, p. 45 - 52
Example 53 2-Methyl-N-(4-(pyrrolidin-1-yl)benzyl)-1,8-naphthyridine-3-carboxamide To a solution of 4-(1-pirrolidino)-benzaldehyde (833 mg, 4.75 mmol) in EtOH (25 ml) hydroxylamine hydrochloride (396.4 mg, 5.70 mmol) and sodium acetate (467.8 mg, 5.70 mmol) were added. The mixture was heated to reflux and stirred for 1.0 hour. The mixture was diluted with EtOAc, washed with H2O, dried (MgSO4), filtered and concentrated to dryness. The residue was then dissolved in anhydrous THF (20.0 ml) under N2. LiAlH4 (1.0 M in THF) (5.7 ml) was slowly added to the solution. The mixture was stirred at r.t. for 24 h. Then it was carefully poured into MeOH (60 ml), the solvent was removed and the residue was suspended in MeOH and filtered. The filtrate was concentrated under reduced pressure yielding 4-(1-Pirrolidino)-benzylamine which was coupled to 2-Methyl-1,8-naphthyridine following the general amide coupling procedure.
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