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6-Hydroxy-1-naphthoic Acid CAS 2437-17-4

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  • Appearance: White to light yellow crystal powde
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: 6-Hydroxy-1-naphthoic Acid Supplement

Basic Info of 6-Hydroxy-1-naphthoic Acid

What is 6-Hydroxy-1-naphthoic Acid?

6-Hydroxy-1-naphthoic acid is widely used as an intermediate in organic synthesis, which is an important raw material for pharmaceutical and dye production. In recent years, tyrosine kinase-targeted drugs (including monoclonal antibodies and small molecule compounds) have been actively developed and applied in various cancers such as hematological malignancies, lung cancer, kidney cancer, colorectal cancer, gastric cancer, and liver cancer.

Deritinib is a small molecule multi-target tyrosine kinase inhibitor targeting VEGFR1, VEGFR2, FGFR1, PDGFRβ, c-Kit, c-Src, and similar drugs have been successfully used in clinical anti-tumor therapy. In non-clinical studies, dalitinib has good efficacy, safety, and pharmacokinetic characteristics, while 6-hydroxy-1-naphthoic acid is a key raw material for a new class of new drugs, dalitinib.

6-Hydroxy-1-naphthoic Acid Uses

6-Hydroxy-1-naphthoic acid can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

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Preparation of 6-Hydroxy-1-naphthoic Acid

  • Report one
    Early literature reports: the preparation method of 6-hydroxy-1-naphthoic acid is to use furoic acid and anisole as starting materials, through Diels-Alder reaction, cyclization, demethylation and other reactions to obtain 6-hydroxy-1-naphthalene formic acid.
    In 1947, Price, Enos and Kaplan et al. reported that 6-methoxy-1-naphthoic acid and 6-methoxy-1-naphthoic acid were synthesized with furoic acid and anisole as raw materials under the catalysis of Lewis acid. 6-Hydroxy-1-naphthoic acid is prepared by demethylation by reflux reaction in hydrobromic acid acetic acid solution, and the total yield is 10.6%-20.7%. In 1941, Long, Burger et al. used 5-methoxy-2-naphthalene nitrile as the starting material, and prepared 6-hydroxy-1-naphthoic acid by hydrolysis and demethylation of hydrobromic acetic acid solution.

  • Report two
    In a 250ml four-neck flask, add 20g furoic acid, 19.3g anisole, and 100ml chlorobenzene, stir and mix; heat the oil bath to an internal temperature of 35-40°C, and slowly add 55.9g anhydrous aluminum trichloride; The reaction was stirred at 75-80 ° C for about 24 hours; cooled, concentrated under reduced pressure and evaporated chlorobenzene; after the distillation was completed, it was lowered to room temperature, and 60 ml of N,N-dimethylformamide was put into the reaction flask, stirred and mixed, and at room temperature , slowly and gradually add 32.1g of anhydrous aluminum trichloride; after feeding, the oil bath is heated to an internal temperature of 135 ° C, and the reaction is kept for 6 hours; Extract with ethyl acetate several times, combine the ethyl acetate extracts, wash with water, pH to weakly acidic; the organic layer is concentrated under reduced pressure, and ethyl acetate is recovered; the residue is decolorized and recrystallized with dilute alcohol water to obtain gray to pale yellow powder 14.6 g of 6-hydroxy-1-naphthoic acid, yield: 43.5%, melting point: 204.5-208.7°C, purity: 98.5%.

Reference

  1. 6-Hydroxy-1-naphthoic acid – PubChem
  2. [Chinese invention] CN201810425189.7 The preparation method of 6-hydroxy-1-naphthoic acid – ChemicalBook

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