HCID 658603, compound → HCID 59570176, compound
Reaction equation
[C:1]([C:5]1[C:6]([OH:14])=[C:7]([CH:11]=[CH:12][CH:13]=1)[CH:8]=[N:9]O)([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.CO.[Pd]>[NH2:9][CH2:8][C:7]1[CH:11]=[CH:12][CH:13]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[C:6]=1[OH:14]Participants
5
Reagents, catalysts & solvents 3
Procedure
3-tert-butyl-2-hydroxybenzaldehyde oxime (550 mg, 2.9 mmol) in EtOAc (10 mL) and MeOH (10 mL) was hydrogenated at balloon pressure in the presence of 10% Pd on carbon (100 mg) for 15 h. The reaction mixture was filtered over celite and concentrated. The residue was dissolved in EtOAc and 0.5 N HCl (10 mL). The layers were separated and the aqueous layer was treated with 1N NaOH solution until pH=9. The resulting aqueous layer was extracted with CHCl3 (3×10 mL). The combined CHCl3 was washed with brine, dried with Na2SO4 and concentrated under reduced pressure to provide to desired product (123 mg, 23%).