N-Cyclopropyl-5-fluoro-2-nitroaniline → 1-N-cyclopropyl-5-fluorobenzene-1,2-diamine
Reaction equation
[CH:1]1([NH:4][C:5]2[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:6]=2[N+:12]([O-])=O)[CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([NH:4][C:5]2[C:6]([NH2:12])=[CH:7][CH:8]=[C:9]([F:11])[CH:10]=2)[CH2:3][CH2:2]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To the title compound from Step D (1.23 g, 6.27 mmol) were added 10% palladium on carbon (0.123 g, 1.16 mmol) and methanol (31.3 mL). The resulting mixture was stirred under an atmosphere of hydrogen at room temperature overnight. The reaction mixture was then filtered through CELITE° using dichloromethane and concentrated under reduced pressure. Purification by flash chromatography on silica gel (0 to 30% ethyl acetate in hexanes) provided the title compound: 1H NMR (500 MHz, CDCl3) δ 6.76 (dd, J=10.9, 2.8 Hz, 1 H), 6.60 (dd, J=8.4, 5.6 Hz, 1 H), 6.34 (ddd, J=11.2, 8.4, 2.8 Hz, 1 H), 4.17 (br s, 1 H), 3.01 (br s, 2 H), 2.42-2.38 (m, 1 H), 0.77-0.72 (m, 2 H), 0.54-0.51 (m, 2 H).