Methyl 3-(4-nitrophenyl)-2-propenoate → Methyl 3-(4-aminophenyl)propanoate

A solution of methyl (E)-3-(4-nitrophenyl)acrylate (S31, 4.10 g, 19.8 mmol) in MeOH (30 mL) and THF (30 mL) was treated with 10% Pd/C (400 mg). The reaction mixture was purged with H2 and was stirred at 25° C. for 10 h. The suspension was filtered through diatomaceous earth and concentrated to afford S32 (3.40 g, 19.0 mmol, 95%) as a yellow solid: 1H NMR (CDCl3, 500 MHz) 6.99 (d, 2H, J=8.2 Hz), 6.63 (d, 2H, J=8.4 Hz), 3.60 (s, 3H), 2.85 (t, 2H, J=7.7 Hz), 2.58 (t, 2H, J=7.7 Hz); 13C NMR (CDCl3, 125 MHz) 173.5, 144.6, 130.5, 129.1, 115.3, 51.5, 36.1, 30.1.

1. customThe reaction mixture was purged with H2
2. filtrationThe suspension was filtered through diatomaceous earth
3. concentrationconcentrated
4. customto afford S32 (3.40 g, 19.0 mmol, 95%) as a yellow solid

ORD-Eintrag

ord-77a0dd304c9441dd91cb47a29775c16c

Quelldatensatz

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08372823B2