Organic Syntheses, CV 3, 664
Submitted by Charles C. Price and Sing-Tuh Voong.
Checked by Richard T. Arnold and Jay S. Buckley, Jr..
1. Procedure
Twenty grams (0.115 mole) of α-nitronaphthalene (Note
1) and
50 g. (0.72 mole) of powdered hydroxylamine hydrochloride are dissolved in
1.2 l. of 95% ethanol contained in a
3-l. flask which is heated in a bath maintained at 50–60°. A filtered solution of
100 g. of potassium hydroxide in 500 g. (630 ml.) of methanol is added gradually with vigorous mechanical stirring (Note
2) over a period of 1 hour. Stirring is continued for an additional hour, and the warm solution is poured slowly into 7 l. of ice water. After the solid has coagulated, it is collected on a filter and washed thoroughly with water. The crude
4-nitro-1-naphthylamine is purified by recrystallization from
500 ml. of 95% ethanol (Note
3). About
12–13 g. (
55–60%) of long golden-orange needles, m.p.
190.5–191.5°, is obtained.
2. Notes
3. Discussion
This preparation is referenced from:
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