HCID 59226503, compound → HCID 59226443, compound

Reaction equation

[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH2:15][CH2:14][CH2:13][CH:12]([N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:26])[CH:11]=1)([O-])=O>CC(O)=O.CO.[Pd]>[NH2:1][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[CH:10]1[CH2:15][CH2:14][CH2:13][CH:12]([N:16]2[C:17](=[O:26])[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]2=[O:25])[CH2:11]1

Participants

Procedure

A solution of 2-[3-(3-nitropyridin-4-yl)cyclohex-2-en-1-yl]-1H-isoindole-1,3(2H)-dione (0.100 g, 0.286 mmol) in AcOH (3.0 mL) was mixed with 10% Pd on carbon (0.046 g, 0.043 mmol) and hydrogenated at 30 psi for 16 h. The reaction mixture was diluted in MeOH (50 mL), filtered and concentrated under vacuum. The residue was dissolved in EtOAc and washed with 1 M NaOH. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give the sub-title compound. LCMS calc. for C19H20N3O2 (M+H)+: m/z=322.2. Found: 322.1.