Acetic Acid → HCID 68467882, compound

Participants

Reaction Steps

To a solution of 6-(4-formylnaphthalen-1-yloxy)nicotinonitrile (Preparation 1) (1.50 g, 5.47 mmol) in DCM (15 mL) was added acetic acid (0.98 mL, 16.42 mmol) and 3-methylbutylamine (1.91 mL, 16.42 mmol). After 1 h NaBH(OAc)3 (3.48 g, 16.42 mmol) and DCM (20 mL) were added. The reaction was stirred at rt for a further 16 h. The mixture was partitioned between DCM (150 mL) and saturated NaHCO3 (200 mL), the organic phase washed with water (200 mL) and dried (MgSO4). Solvent removed in vacuo. To the residue was added ether (10 mL) followed by 4M HCl in dioxane (1.0 mL, 4.0 mmol). A further 40 mL of ether was added and the resulting precipitate filtered and dried under vacuum to give the title compound: RT=2.84 min; m/z (ES+)=346.2 [M+H]+.

Provenance & Evidence