Dimethylformamide → 2-Amino-1-naphthol

Participants

Reaction Steps

To dry DMF (60 mL) were added Pd2 dba3-CHCl3 (0.04 g, 0.038 mmol), and triethyl phosphite (0.04 mL, 0.229 mmol), and the solution was aged for 5 minutes at room temperature. The mixture was degassed with 3 nitrogen/vacuum cycles and stirred for 30 minutes until solution became yellow. Then the naphtholamine 145 (0.20 g, 0.80 mmol), CPI 5 (0.52 g, 0.88 mmol), and 2,6-lutidine (0.046 mL, 0.4 mmole) were added to the reaction solution and the resulting mixture was aged for 3 hours. Solvent was removed under reduced pressure and crude residue was purified by flash column chromatography with 97:3 CH2Cl2/MeOH to afford the desired couple product 146 as a yellow oil (0.47 g, 82% yield).

Provenance & Evidence