Methanol → (E)-3-(4-Amino-phenyl)-2-methyl-acrylic acid methyl ester

α-Methyl-4-nitrocinnamic acid (53 mg, 0.25 mmol) was dissolved in EtOAc and MeOH and a solution of CH2N2 in Et2O was added until a persistent yellow color was observed. A couple of drops of AcOH were added to destroy the excess CH2N2. The mixture was diluted with EtOAc and the organic layer was washed with H2O, aqueous NaOH (1N) and brine, dried over anhydrous MgSO4 and concentrated to dryness. The residue was re-dissolved in EtOH (2 mL), SnCl2-2H2O (289 mg, 1.28 mmol) was added and the reaction mixture was heated to reflux for 1 h. The mixture was cooled to RT, diluted with EtOAc and quenched by the addition of aqueous, saturated NaHCO3. The organic layer was separated, washed with brine, dried over anhydrous MgSO4 and concentrated to dryness to give the title compound (40 mg) as a yellow solid.

1. customto destroy the excess CH2N2
2. additionThe mixture was diluted with EtOAc
3. washthe organic layer was washed with H2O, aqueous NaOH (1N) and brine
4. dry with materialdried over anhydrous MgSO4
5. concentrationconcentrated to dryness
6. dissolutionThe residue was re-dissolved in EtOH (2 mL)
7. temperaturethe reaction mixture was heated
8. temperatureto reflux for 1 h
9. customquenched by the addition of aqueous, saturated NaHCO3
10. customThe organic layer was separated
11. washwashed with brine
12. dry with materialdried over anhydrous MgSO4
13. concentrationconcentrated to dryness

ORD record

ord-d2b543a4f10a4d2f99f2374450751f0c

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576079B2