Acetone → HCID 54250348, compound

Temperature

0 °C

Sodium triacetoxyborohydride (27.9 g, 134 mmol) is added portionwise over 45 minutes to a 0° C. solution of 2-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-(2-methoxy-phenyl) aniline (14.51 g) as an amber oil which is used without further purification: 1H NMR (300 MHz, CDCl3) δ6.91 (t, 1H, J=7.6), 7.01 (d, 1H, J=7.6), 6.68 (t, 2H, J=7.9), 3.88 (s, 3H), 3.66 (m, 1H, J=6.8), 1.28 (d, 6H, J=6.8).

1. customThe organics were removed
2. additionthe residual aqueous phase diluted with water (30 mL)
3. extractionextracted into ethyl acetate (3×50 mL)
4. washThe combined organics were washed with water (2×100 mL), brine (50 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo

ORD record

ord-6eb44edc23d84c5aaf47dee198ca67b2

Source dataset

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05859007