Methanol → HCID 86689305, compound

Reaction equation

CO.[N+:3]([C:6]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[CH:9]=[CH:8][C:7]=1[NH:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[C:20]#[N:21])([O-])=O>[Pt]=O.O1CCCC1>[NH2:3][C:6]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[CH:9]=[CH:8][C:7]=1[NH:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[C:20]#[N:21]

Participants

Procedure

To a methanol (10 mL) and anhydrous tetrahydrofuran (30 mL) solution of 3-(1-nitro-5,6,7,8-tetrahydronaphthalen-2-ylamino)benzonitrile (1.52 g, 5.17 mmol was added platinum oxide (50 mg), and the mixture was hydrogenated for 29 hours at room temperature under atmospheric pressure. After removal of the catalyst by filtration, the solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (chloroform) to give the titled compound as yellow powder (747 mg, yield 55%).