The author of 《Convenient method for the preparation of hydroxynaphthoic acids》 were Cason, James. And the article was published in Journal of the American Chemical Society in 1941. Recommanded Product: 72016-73-0 The author mentioned the following in the article:
The procedure of Butler and Royle (C. A. 17, 3182) for the synthesis of 4,2-C10H6(CO2H)OH gave very poor yields; various modifications produced the acid in satisfactory yields by way of the same intermediates. 4,2,5-C10H5(NH2)(CO2H)2(345 g.), 390 g. NaOH, 135 g. Zn and 900 cc. H2O, refluxed for 22 h., give 81-7% of 4,2-C10H6(NH2)SO3Na; distillation with KCN at about 500° gives 10-13% of 4,2-C10H6(NH2)CN, m. 125.5-6° (all m. ps. corrected); K4Fe(CN)6 (used by B. and R.) gives only 1-4%; CuCN could not be used because of foaming; a mixture of KCN with NaCN or K4Fe(CN)6 did not give better yields; hydrolysis with a mixture of 10 cc. AcOH and 2.5 cc. 70% H2SO4 gives 86% of 4,2-C10H6(NH2)CO2H, m. 215-16°; the diazo reaction did not give a good yield of 4,2-C10H6(OH)CO2H (I) but heating 4.5 g. of amine and 45 cc. 10% H2SO4 at 195-200° for 4 h. gives 90.5% of I, m. 225-6° (B. and R. give 182-3°); the Ac derivative (II) m. 211.5-12.5° (44° above reported value). II and PCl5, heated at 100° for 25 min., give 88% of 4-acetoxy-2-naphthoyl chloride (III), m. 96-8° and remelting at 99-9.5°; catalytic reduction in boiling xylene (Rosenmund’s method) gives 50-75% of 4-acetoxy-2-naphthaldehyde, m. 113.2-14.2°; semicarbazone (III), m. 230° (decomposition). Hydrolysis with N H2SO4 for 1 h. gives 63% of 2-hydroxy-2-naphthaldehyde (IV), buff, m. 169.5-70°. No definite product could be obtained on Wolff-Kishner reduction of III. Catalytic reduction (Cu-Cr catalyst) of IV gives 4,2-C10H6(OH)Me, m. 90-1°. The Na salt of 1,6-Cleve’s acid yields 9.5-10% of 5,2-C10H6(NH2)CN, m. 143.5-4°; hydrolysis gives 83.5% of 5,2-C10H6(NH2)-CO2H, m. 291-2°; 10% H2SO4 at 220-5° for 4 h. gives 67% of 5,2-C10H6(OH)CO2H, m. 215-16° (Ac derivative, m. 215-16°). 6-Amino-2-naphthonitrile, pale greenish yellow, iridescent plates, m. 199-9.5° (1.5% yield); with K4Fe-(CN)6 the yield is only 0.2%. 6,2-C10H6(OH)CO2H, m. 243-4°, 53.5% (Ac derivative, m. 223-4°). 5,1-C10H6(NH2)CN, m. 139.5-40°, results in 20% yield and 5,1-C10H6(OH)CO2H is formed in 53-7% yield. In the experiment, the researchers used 5-Amino-1-naphthonitrile(cas: 72016-73-0Recommanded Product: 72016-73-0)
5-Amino-1-naphthonitrile(cas: 72016-73-0) belongs to anime. Hydrogen peroxide (H2O2) and peroxy acids generally add an oxygen atom to the nitrogen of amines. With primary amines, this step is normally followed by further oxidation, leading to nitroso compounds, RNO, or nitro compounds, RNO2. Secondary amines are converted to hydroxylamines, R2NOH, and tertiary amines to amine oxides, R3NO.Recommanded Product: 72016-73-0
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts