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

Boiling point:

437.6±55.0 °C(Predicted)

Density 

1.29±0.1 g/cm3(Predicted)

solubility 

DMSO (Slightly)

pka

3.45±0.10(Predicted)

form 

Solid

color 

Pale Orange to Brown

InChI

InChI=1S/C10H12N4O/c1-14-6-12-10(13-14)7-4-3-5-8(11)9(7)15-2/h3-6H,11H2,1-2H3

InChIKey

FIAZRZSVFOMYSD-UHFFFAOYSA-N

SMILES

C1(N)=CC=CC(C2N=CN(C)N=2)=C1OC

2-methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)aniline Usage And Synthesis

Chemical Properties

white solid

Uses

2-Methoxy-3-(1-methyl-1H-1,2,4-triazol-3-yl)aniline is used in the preparation of pyridazines which is a heterodimeric cytokines modulators for treatment of diseases.

Synthesis

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.