Hexanal → HCID 86653144, compound

Participants

Reaction Steps

To a stirred solution of 6-{[({[3-(methylsulfanyl)phenyl](1-methyl-1H-tetrazol-5-yl)methylene}amino)oxy]methyl}pyridin-2-amine (134 mg, 0.38 mmol) in dry dichloromethane (5 mL) were added capronaldehyde (52.9 mg, 0.53 mmol) and sodium triacetoxyborohydride (151 mg, 0.68 mmol) at room temperature. After stirring at room temperature for 20 h, the reaction mixture was diluted with dichloromethane (10 mL) and aq. NaHCO3 (10 g/L, 10 mL) was added. After phase separation, the organic layer was washed with water, dried over MgSO4 and concentrated in vacuo. Purification on silica gel afforded N-hexyl-6-{[({[3-(methylsulfanyl)phenyl](1-methyl-1H-tetrazol-5-yl)methylene}amino)oxy]methyl}pyridin-2-amine as a colourless oil [115 mg, yield 69%; HPLC/MS: m/z=440 (M+H); logP(HCOOH)=2.78].

Provenance & Evidence