Isoquinoline, 3,4-dihydro-6,7-dimethoxy-1-methyl

Oimethoxy-1 -methyl-3,4-dihydrolsoquinoline Isoquinoline, 3,4-dihydro-6,7-dimethoxy-1-methyl- (8,9) (4721-98-6)... 

Isoquinoline, 2-acetyl-l, 2,3,4-tettahydro-6,7-dimethoxy-l-inethylene-, 4 Isoquinoline, 2-benzoyl-l -benzy 1-1-cyano-1,2-dihydro- [1-Isoquinolinecarbo-mtrile, 2-benzoyl-l, 2-dihydro-l -(phenjlmethyl)-), 23 Isoquinoline, 2-benzoyl-l -cyano-1,2-di-hydro l-Isoquinohnecarbomtrile, 2-ben2oyl-l, 2-dihydro-], 20 ISOQUINOLINE, 1-BENZYL- [ISOQUINOLINE, HPHENYLMFTHYL)-], 19 Isoquinoline, 3,4-dihydro-6,7-dimethoxy-l-methyl-, 4... 

R,5 S)-2-[(2-bromomethylphenyl)methyl -2,5-dihydro-5-mpropyi-3,6-dimethoxy-2-meth ipyrazme >97% de 6 (3, 11 aR)-3,4,6, t t-tetrahydro-3-isoprop I-l-methoxy-U a-methyl-4-oxopyrctzino[l, 2-b isoquinoline yield 75% 97% de... 

Isoquinoline, 1,2,3,4-tetrahy dro-2-methyl-l-(2-phenylethyl)-, 56, 7 Isoquinolines, alkylation of, 56, 19 Isoquinolinium, 2-ethyl-3,4-dihydro-6,7-dimethoxy-1-phenyl-, iodide, 56, 7 ISOXAZOLE, 3-(4-chlorophenyl)-5-(4-methoxyphenylK 55, 39 Isoxazole, 5-(4-chloropher,yl)-3-(4-meth-oxyphenyl)-, 55, 42... 

This plant yielded the first 1-phenyltetrahydroisoquinoline alkaloid to be found in nature. Spectral data indicated that it was l-(3,4-methylenedioxyphenyl) -2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroiso -quinoline, C19H29O4N (mp 101° [ajj) -t-54°) and a synthesis of the diform confirmed this structure (XLVI). The amide resulting from the reaction of piperonoyl chloride with 3,4-dimethoxyphenethylamine was cyclized by means of phosphorus oxychloride. The resulting dihydro-isoquinoline was converted to methiodide and the latter reduced with sodium borohydride. The resulting dZ-base (mp 117°) was identical in spectral properties with the natural alkaloid 66). 

Nakada and Nishihara (51) synthesized carnegine by suspending veratryl-acetoxime in toluene and treating with POCI3, obtaining 1-methyl-6,7-dimethoxy-3,4-dihydro-isoquinoline. Catalytic reduction of the methyl methosulfate of this compound yielded carnegine. 

A mixture of l-acetonyl-6,7-dimethoxy-3,4-dihydroisoquinoline and POClg in benzene refluxed 20 min. on a steam bath crude 2-methyl-8,9-dimethoxy-5,6-dihydro-2H-isoxazolo[3,2-a]isoquinoline (Y ca. 100%), 1 g. dissolved in ethanol, acidified with HCl, and hydrogenated 0.5 hr. with PtOg 1 g. l-(2-hydroxypropyl)-6,7-dimethoxy-l,2,3,4-tetrahydroisoquinoline. N. Itoh, Chem. Pharm. Bull. 8, 441 (1960). 

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