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Vitamin K


DATA No : VVK0017 INFORMANT : Tetsuya Nakamura

NAME : 4-Amino-2-methyl-1-naphthalenol / 4-amino-2-methyl-1-naphthol / 1-hydroxy-2-methyl-4-aminonaphthalene / 2-methyl-4-amino-1-hydroxynaphthalene / 2-methyl-4-amino-1-naphthol / 3-methyl-4-hydroxy-1-naphththylamine.

COMMON NAME: Vitamin K5 / Synkamin base / Vitamin K5 base.
SYMBOL:
FORMULA: C11H11NO MOL.WT (average) : 173.211


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CHEMICAL SYNTHESIS
By heating, 187.5 g of stannous chloride are dissolved in 800 cm3 of concentrated hydrochloric acid (d=1.19). To the hot solution a suspension of 60 g of the monoxime of 2-methyl-1,4-naphthoquinone in 250 cm3 of warm concentrated hydrochloric acid is added. The desired hydrochloride separates out and the reaction mixture stirred for about 5 minutes. When the temperature has fallen to 50degC the substance is filtered rapidly (Schott G3 glass filter) and washed three times with 125 cm3 of 4n hydrochloric acid. The crude compound is dissolved in a solution of 30 g of potassium metabisulphite in 750 cm3 of water, and after treating with charcoal, the pure hydrochloride is precipitated by means of 600 cm3 of concentrated hydrochloric acid to which 6 g of potassium metabisulphite have been added. The substance is filtrated by suction (glass filter), washed three times with 100 cm3 of 4n hydrochloric acid, then with 60 cm3 of alcohol and dried in vacuo over potassium hydroxide. Yield 50 g (75%).(Ref. 0041)
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REFERENCES
[0041]
AUTHOR:Verdstra, H., and Wiardi, P. W.
TITLE:Water soluble antihemorrhagic substances I. Synthesis of 2-methyl-1,4-aminonaphthol-1 hydrochloride and 2-methyl-1,4-diaminonaphthalene dihydrochloride, the water soluble synthetic vitamins K5 and K6.
JOURNAL:Rec. Trav. Chim.
VOL:62 PAGE : 75 -84 (1943)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.