Some phenolic derivatives of [beta]-phenylethylamine / by George Barger and Arthur James Ewins.

  • Barger, George, 1878-1939.
Date:
1910
Catalogue details

Licence: Attribution 4.0 International (CC BY 4.0)

Credit: Some phenolic derivatives of [beta]-phenylethylamine / by George Barger and Arthur James Ewins. Source: Wellcome Collection.

Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.

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    Preparation of 4-Uydroxy-fi-xa-tolylethylamine, CHg_ OH<^ \CII2-CH2*NH2. CH^ p-Nitro-m-tolylacetonitrile, N02<^ X/CH3*CN.—Ten grams of m-tolylacetonitrile (Senkowski, Moncttsh., 1888, 9, 854) were dropped i into 40 c.c. of nitric acid (D 1*5) at a temperature below -5°. The acid solution was then poured into water and extracted with ether. After washing with sodium carbonate, drying, and distilling, a fractioni boiling at 201—205°/22 mm. was collected, which solidified, and on. crystallisation from ether and light petroleum molted at 52°. The yield was 80 per cent, of the theoretical: 0-1584 gave 0-3554 CO., and 0-06G5 H20. C = 61-2 ; H = 4-6. C9Hs02N2 requires C=6T4; H = 4-5 per cent. p - Amino - m - tolylacetonilrile, NH2-C8rigMe-CH2-CN.—p - Nitro- wi-tolylacetonitrile (19 grams) was dissolved in alcohol (240 c.c.), tin- foil (25 grams), and then gradually concentrated hydrochloric acid] (120 c.c.) was added. The temperature was at first kept, below 60°,. finally being raised to 100°. After extraction with ether, the base was- distilled, and 8 5 grams (60 per cent.) boiling at 175—185°/20 mm. were obtained. On crystallisation from bonzene, the substauce molted I at 87°: 01552 gave 0-4204 C02 and 0 0902 HsO. C •= 73‘9 ; H = 6 5. C9H10N2 requires C = 74-0 ; H = 68 per cent. The hydrochloride, prepared by adding alcoholic hydrogen chloride to the ethereal solution of the base, melts at 247—248°: 0-2082 gavo 0-1620 AgCl. Cl = 19-3. C9II10N„,HC1 requires Cl = 19-4 per cent. The oxalate melts at 164—165° : 0 1884 gavo 24 c.c. N2 (moist) at 20° and 768 mm. N = 14*7. (C9H10N2)2,H2C2O4 requires N = 14 7 per cent. p-Hydroxy-m-tolylacetonitrile, OH-CGH3Mo-CIT2-CN.—39 Grams of sodium nitrite dissolved in a little water were slowly added to a boiling, solution of 8-5 grams of the amino-compound dissolved in 200 c.c. ol dilute sulphuric acid (210 c.c. of water and 17 c.c. of concentrated sulphuric acid). On extracting the acid solution with ether, 2-5 grams (30 per cent.) of a substance were obtained, which distilled at 162—164°/2 mm. and crystallised in the receiver. It crystallises froin benzene in leaflets melting at 84°: