Lithium → N-methyl-2-phenoxyaniline

Temperature

65 °C

To a solution of 2-phenoxy-N-(t-butoxycarbonyl)aniline (1.43 g, 5.0 mmol) in anhydrous tetrahydrofuran (50 ml) was added lithium aluminumhydride (10 ml, 10.0 mmol, 1.0 M solution in tetrahydrofuran) at −10° C. The mixture was then refluxed at 65° C. overnight. The reaction mixture was quenched with slow addition of MeOH (10 ml) and concentrated under reduced pressure. The reaction mixture was then 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 over (Na2SO4), concentrated under reduced pressure to give N-methyl-2-phenoxyaniline (0.94 g, 94.0%) as a pale yellow oil. The product was confirmed by LC-MS and subjected to next reaction without further purification.

1. customThe reaction mixture was quenched with slow addition of MeOH (10 ml)
2. concentrationconcentrated under reduced pressure
3. additionThe reaction mixture was then poured into water (50 ml)
4. extractionextracted with ethyl acetate (3×100 ml)
5. washwashed with brine (2×100 ml)
6. dry with materialdried over (Na2SO4)
7. concentrationconcentrated under reduced pressure

ORD record

ord-0b5c73fd79424ea5961175e088e884e6

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07384967B2