ChemicalBook CAS DataBase List 2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)aniline

2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)aniline synthesis

9synthesis methods

Product Name:2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)aniline
CAS Number:1609394-10-6
Molecular formula:C10H12N4O
Molecular Weight:204.23

To a high pressure reactor flushed with nitrogen were charged methanol (8.0 kg/kg) and Compound 6 (1.0 kg). With careful exclusion of oxygen, sodium bicarbonate (0.6 kg/kg, 2.0 equiv.) and Pd/C (10% loading, 50 % wet, 0.02 kg/kg) were added. The reactor was pressurized with hydrogen (41-46 psi), and the reaction mixture was aged at 20 °C for 6 h then heated to 45 °C and aged till reaction reached completion. The reactor was flushed with nitrogen, and the reaction crude was filtered to remove Pd/C. Methanol (5 kg/kg) was used to aid the transfer. The combined filtrates were distilled under vacuum until total volume became approximately 2.5 L/kg. Water (10 kg/kg) was added, and the crude was distilled under vacuum until total volume became approximately 2.5 L/kg. The crude was heated to 70 °C. Brine (25 wt%, 9.0 kg/kg) was added, and the resulting crude was agitated for 6 h at 70 °C. After cooling down to 0 °C, the crude was further aged for 6 h. Product was isolated by filtration. The cake was washed with brine (pre-cooled to 0 °C, 25 wt%, 2.0 kg/kg), and dried under vacuum at 45 °C. 2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)aniline was isolated in 99 AP and 88% yield.
synthesis of 2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)aniline

synthesis of 2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)aniline

3-(2-methoxy-3-nitrophenyl)-1-methyl-1H-1,2,4-triazole

1609394-08-2
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2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)aniline

1609394-10-6
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Yield:1609394-10-6 95.57%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in methanol; for 24 h;

Steps:

296 Synthesis of compound 296.3

To a compound of 296.2 (3g, 12.8mmol, 1.Oeq) in MeOH (30mL) 10% Pd/C (1.5g) was added. Hydrogen was purged through the reaction mixture for 24h. After completion of the reaction, the reaction mixture was filtered through celite bed, washed with MeOH and concentrated in vacuo to obtain crude product. This was purified by column chromatography using 20% ethyl acetate in hexane to obtain pure 296.3 (2.5g, 95.57%). MS(ES):m/z 205.84 [M+H]t

References:

WO2018/75937,2018,A1 Location in patent:Paragraph 001348; 001351

1609393-90-9 Synthesis