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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 2, 1972 - Issue 3
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Original Articles

8-Methxlcorxpallihe and its O-Metbzlzzher: A Facile Sxhthesis of 8-Methxl Substituted-6, 7- Dimethoxy Tetrahsdroisoquxnolines

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Pages 171-174 | Received 06 Mar 1972, Published online: 26 Jan 2007

References

  • Harley-Maaon , J. , Howard , A. S. , Taylor , W. I. , Veraengo , M. J. , flick , I. R. C. and Clezy , P. S. 1967 . J. Chem. Soc. (C) , : 1948
  • Aoki , K. and Barley-Mason , J. 1967 . J. Chem. Soc. (C) , : 1957
  • Poppelsdorf , F. and Bolt , S. J. 1954 . J. Chem. Soc. , : 1124
  • Broasi , A. , O'Brien , J. and Teitel , S. 1970 . Org. Prep. Procedures , 2 : 281
  • Burger , A. and Foggio , R. D. 1956 . J. Amer. Chem. Soc. , 78 : 4419
  • Condensation of 3, 4-dimethoxy-2-methylbenzaldehyde with aminoacetaldehyde dimethylacetal provided K-(3, 4-di-methoxy-2-methylbenzyl)aminoacetaldehyde dimethylacetal (bp 135°/0.2 mm: nD 25 1.5770) which was cyclized by treatment with acid followed by catalytic hydrogenation. The reeulting 6, 7-dimethcncy-8-methyl-l, 2, 3, 4-tetrahydxoiso-quinoline hydrochloride (mp 199–200”) upon reductive condensation with formaldehyde afforded 6, 7-damethoxy-2, 8-dimethyl-1, 2, 3, 4—tetrahydroisoquinoline which was identical in mmp, tic, and nmr with S.
  • All melting points (corrected) were taken in open capillary tubes with a Thomas-Hoover melting apparatus. Nmr spectra were obtained with a Varian Hft-100 spectrometer using tetramethylsilane as the internal standard. Extracts of products were washed with water and dried over anhydrous sodium sulfate prior to evaporation. Reported yields were not optimized and are of isolated products homogeneous to tic. All compounds gave acceptable elemental analyses

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