1-(2-fluoro-6-methoxy-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole → 3-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([O:11][CH3:12])[C:3]=1[N:13]1[CH:17]=[N:16][C:15]([CH3:18])=[N:14]1>[Pd].CO>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([O:11][CH3:12])[C:3]=1[N:13]1[CH:17]=[N:16][C:15]([CH3:18])=[N:14]1)[NH2:8]Participants
4
Procedure
Step S (2): 10% Palladium on carbon (0.776 g, 0.730 mmol) was added under an atmosphere of nitrogen to a chilled (ice-water bath) solution of 1-(2-fluoro-6-methoxy-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole (1.84 g, 7.30 mmol) dissolved in methanol (150 mL). The flask was repeatedly evacuated and flushed with hydrogen gas (double balloon). The resulting mixture was allowed to warm to rt and left to stir for 18 h under the hydrogen atmosphere. The vessel was subsequently purged with nitrogen gas. The crude reaction mixture was filtered through a short plug of diatomaceous earth (Celite®). The reaction vessel and the Celite® were rinsed with fresh methanol. The combined filtrates were concentrated in vacuo. The residue was dried under high vacuum overnight to afford 3-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)aniline (2.17 g, quantitative % yield) as a blackish/gray solid. LC-MS (M+H)+ 223.2. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 8.02 (s, 1 H), 6.11 (dd, J=11.1, 2.3 Hz, 1 H), 6.06 (d, J=1.5 Hz, 1 H), 4.04 (br. s., 2 H), 3.74 (s, 3 H), 2.48 (s, 3 H).