2-(4-Methyl-3-nitrobenzyloxy)tetrahydropyran → 2-Methyl-5-(tetrahydropyran-2-yloxymethyl)phenylamine
Reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][O:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][O:9]2)=[CH:4][C:3]=1[N+:16]([O-])=O>C(O)C.[Pd]>[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][O:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][O:9]2)=[CH:4][C:3]=1[NH2:16]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
The solution of 12.3 g of 2-(4-methyl-3-nitrobenzyloxy)tetrahydropyran in 150 ml of ethanol is hydrogenated in the presence of 1.25 g of 10% Pd/C over 24 hours. The reaction mixture is filtered and the filtrate is concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.19 (1:2 EtOAc-heptane); Rt=2.72.