Tetrahydrofuran → HCID 15980985, compound
Reaction equation
[CH3:1][O:2][C:3](=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)[C:4]([OH:6])=[O:5].C1COCC1>CO.[Pd]>[CH3:1][O:2][CH:3]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=1)[C:4]([OH:6])=[O:5]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
2-Methoxy-3-(4-nitrophenyl)acrylic acid (6.7 g, 30 mmol) was taken up in methanol (700 ml) and THF (300 ml) and 10% Pd on C (wet basis) (0.67 g) was added. The mixture was hydrogenated at 45 psi for 43 mins, followed by repeated refills to 45-48 psi every hour for 3 hr and finally 48 psi for 18 hr. The resulting suspension was filtered through GF/F filter paper and the filter residue washed with MeOH (200 ml). The filtrates were concentrated to an off-white solid. The solid was slurried in IMS (75 ml) at 20° C. for 1.5 hr, filtered, and washed with IMS/heptane (1:2) (20 ml) and dried on the filter for 1 hr to afford (±)-2-methoxy-3-(4′-aminophenyl)-propionic acid as an off-white solid (5.1 g, 88% yield)