Laudanine methyl ether

Isothebaine (= 1-Hydroxy-2,1 1-dimethoxyaporphine) (aporphine isoquinoline) Laudanosine (= Laudanine methyl ether) (benzylisoquinoline)... 

In a similar attempt, Decker and Eichler reduced A -methylnor-papaverinium phenolbetaine (VIII) with tin and hydrochloric acid and obtained i/i-laudanine, m.p. 112°, pierate, m.p. 162-3°, which was subsequently investigated by Spath and Epstein, who showed that on methylation it furnished dMaudanosine and that the ethyl ether on energetic oxidation yielded veratric acid (3 4-dimethoxybenzoic acid) and the methyl ethyl ether of nor-m-hemipinic acid. This clearly indicated that the free hydroxyl group was in the woquinoline nucleus, and its position was determined by the fact that on mild oxidation 7-methoxy-6-ethoxy-l-keto-2-methyl-l 2 3 4-tetrahydrowoquinoline, m.p. 95-6°, was produced, and on this basis these authors assigned formula (IX R = H R = CH3) to -laudanine. 

Methylation with methyl iodide (93) or diazomethane (86) yields dl-laudaiiosine (XIII). Likewise, ethylations with ethyl iodide, ethyl sulfate (84), or diazoethane furnish 3 -ethyllaudanine. Oxidation of this ethyl ether ruptures the molecule, and Spath (86) was able to isolate 3-ethoxy-4-methoxybenzoic acid from the reaction mixture, thus locating the position of the hydroxyl group in laudanine. 

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