7-Methoxyindazole Chemical Properties

Melting point:

91-92 °C

Boiling point:

312.5±15.0 °C(Predicted)

Density 

1.244±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

13.33±0.40(Predicted)

color 

Brown

Safety Information

HS Code 

2933998090

7-Methoxyindazole Usage And Synthesis

Uses

7-Methoxy-1H-indazole is an inhibitor of neuronal nitric oxide synthase.

Synthesis

GENERAL STEPS: To a solution of N-(2-methoxy-6-methylphenyl)acetamide (9.28 g, 51.8 mmol) in ethyl acetate (100 mL) was added sequentially acetic anhydride (14.7 mL, 156 mmol), tetrabutylammonium bromide (0.84 g, 2.61 mmol), potassium acetate (10.16 g, 104 mmol), and isoamyl nitrite ( 9.1 mL, 67.7 mmol). The reaction mixture was heated to reflux for 9 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. To the residue, 6 N aqueous sodium hydroxide solution (100 mL) was added and stirred for 1 h at room temperature. Subsequently, the pH of the mixture was adjusted to 7-8 with 3 N hydrochloric acid and extracted with chloroform. The organic layers were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate = 3/1→1/1) to afford 7-methoxy-1H-indazole (3.95 g, 51% yield).1H-NMR (DMSO-d6) δ: 3.94 (3H, s), 6.82 (1H, d, J = 7.5 Hz), 7.02 (1H, dd, J = 8.0, 7.5 Hz), 7.30 (1H, d, J = 8.0 Hz), 8.01 (1H, d, J = 1.5 Hz), 13.27 (brs, 1H).

References

[1] Patent: EP1514869, 2005, A1. Location in patent: Page/Page column 83
[2] Journal of the American Chemical Society, 1954, vol. 76, p. 1176

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