Synthesis of 4:6-dimethoxy-2-beta-methylaminoethylbenzaldehyde / by Arthur H. Salway.

  • Salway, Arthur H. (Arthur Henry)
Date:
[1911?]
Catalogue details

Licence: In copyright

Credit: Synthesis of 4:6-dimethoxy-2-beta-methylaminoethylbenzaldehyde / by Arthur H. Salway. Source: Wellcome Collection.

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    0-1050 gave 0*2498 C02 and 0*0575 H20. C = 64’8; H = 61. 0-2331 „ 0-0990 AgCl. Cl = 10’5. Ci8H2o03NCl requires 0 = 64*8; H = 60; 01 = 10*6 per cent. The chlorinated base corresponding with this phenylacetyl compound yielded a hydrochloride, which crystallised in radiating clusters of colourless needles, melting at 188°: 0-1096 gave 0-1930 C02 and 0-0618 H20. C=48‘0; H = 63. 0*1510 „ 0*0858 AgCl. Cl (as hydrochloride) = 14*1. C10H14O2NCl,HCl requires 0 = 47*6; H = 6-0; Cl (as hydrochloride) = 14*1 per cent. It is thus evident that in the above experiment one atom of hydrogen had been substituted for one atom of chlorine, and since the chlorinated compound yielded, on oxidation, a monochloro- dimethoxybenzoic acid (m. p. 181—182°) of the formula C9H904C1 (neutralisation value: Found: 254*6. Calc., 259*1), it follows that the chlorine must be present in the nucleus. The above compound, melting at 188°, is therefore the hydrochloride of ,8-2(4)-chloro- 3:5-dimethoxy'phenylethylamine. 6 :&-Dimethoxy-1-benzyl-?) : ^-dihydro\soquinoline (VII, p. 1321). A quantity (10 grams) of phenylacetyl-/3-3:5-dimethoxyphenyl- ethylamide was dissolved in xylene, the solution heated to boiling, and phosphoric oxide added in small quantities, with agitation, until a small portion of the xylene solution gave no precipitate of unchanged substance with light petroleum. The solvent was then decanted from the yellow mass of phosphorus compound, and the latter decomposed by warming with an excess of dilute hydro¬ chloric acid. The acid liquid was filtered to remove a little resinous matter, then rendered alkaline, and extracted with ether. After washing with water, the ethereal solution was shaken with small portions of dilute hydrochloric acid until no further basic matter was removed. The extracts were then united, and concentrated to a small volume, when an almost colourless, crystalline hydrochloride was deposited, which was collected and purified by recrystallisation from a mixture of alcohol and ethyl acetate. The yield of pure substance amounted to 8 grams: 1-6464 lost, at 110°, 0-1678 H,0. H2O = 10-2. C18H2o02NC1,2H20 requires II2O = 10*2 per cent. 0-1060*gave0-2652 C02 and 0*0643 H20. 0=68*2; H = 67. 0-4730* „ 0*2140 AgCl. Cl = 11*2. C18H20O2NCl requires C = 68*0; H = 63; Cl = ll*2 per cent. 6.: S-Dimethoxy-l-b efisyl-Z : 4=-dihydroi$oqmnoline hydrochloride is * Anhydrous substance.