Acetone → HCID 10966671, compound

Participants

Reaction Conditions

Reaction Steps

Sodium triacetoxyborohydride (27.9 g, 134 mmol) is added portion wise over 45 minutes to a 0° C. solution of 3-methoxyaniline (12.5 g, 101 mmol) in THF (100 mL), acetone (7.82 mL, 106 mmol) and acetic acid (5.9 mL) and the resultant mixture is allowed to attain RT overnight. The reaction mixture is cooled to 0° C. and then water (50 mL) is added slowly followed by 50% aqueous sodium hydroxide solution (20 mL) and the resultant mixture stirred for 1.5 h. The organics were removed and the residual aqueous phase diluted with water (30 mL) and extracted into ethyl acetate (3×50 mL). The combined organics were washed with water (2×100 mL), brine (50 mL), dried (MgSO4), and concentrated in vacuo to afford N-Isopropyl-N-(3-methoxy-phenyl) aniline (16.22 g) as a brown oil which is used without further purification: 1H NMR (300 MHz, CDCl3) δ7.13 (t, 1H, J=8.0), 7.01 (dt, 2H, J=9.7, 1.9), 6.19 (s, 1H), 3.80 (s, 3H), 3.62 (m, 1H, J=6.8), 1.06 (d, 6H, J=6.8).

Provenance & Evidence