Acetic Acid → N-isopropyl-2-phenoxyaniline

To a solution of 2-phenoxyaniline (0.93 g, 5.0 mmol) in dichloroethane (50 ml) was added anhydrous acetone (0.73 ml, 10.0 mmol) and acetic acid (0.1 ml, 2.0 mmol). The mixture was stirred for 30 min, and sodium triacetoxyborohydride (3.18 g, 15.0 mmol) was added in one portion. The reaction mixture was stirred overnight at ambient temperature. The reaction mixture was quenched by slow addition of MeOH (10 ml) and concentrated under reduced pressure. The residue was poured into water (50 ml) and extracted with ethyl acetate (3×100 ml). Organic extracts were combined and washed with brine (2×100 ml) and dried (Na2SO4), concentrated under reduced pressure to give N-isopropyl-2-phenoxyaniline (1.05 g, 91%) as colorless oil.

1. stirringThe reaction mixture was stirred overnight at ambient temperature
2. customThe reaction mixture was quenched by slow addition of MeOH (10 ml)
3. concentrationconcentrated under reduced pressure
4. additionThe residue was poured into water (50 ml)
5. extractionextracted with ethyl acetate (3×100 ml)
6. washwashed with brine (2×100 ml)
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-1caf0552fb9345df815a0cda6d91f712

Quelldatensatz

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07384967B2