Dichloromethane → HCID 22504041, compound
Reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[CH2:12][CH:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-])=O)[CH3:14].C(Cl)Cl>C1COCC1.[Ni]>[CH3:14][CH:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH2:22])[CH2:12][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[CH3:1]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
2-Methyl-1-[2-(2-nitro-phenoxy)-propyl]-naphthalene (1.51 g, 4.70 mmol) was shaken with Rainey nickel (0.5 g) in THF (50 mL) at 49.0 psi H2 for 5.4 hours. TLC analysis (silica, CH2Cl2) indicated complete consumption of starting material. The reaction mixture was filtered and concentrated to give 2-[1-methyl-2-(2-methyl-naphthalen-1-yl)-ethoxy]-phenylamine in quantitative yield. MS (APCI) m/z 292.1 (M+H).