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Differentiation of isomeric 1,2-dihydroisoquinolin-4(3H)-ones by proton magnetic resonance of their 4-benzyl derivatives

✍ Scribed by Roger D. Waigh

Publisher
John Wiley and Sons
Year
1980
Tongue
English
Weight
137 KB
Volume
13
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

Reaction of a 3,3‐dimethyl‐1,2‐dihydroisoquinolin‐4(3__H__)‐one with a benzyl Grignard reagent gives a 4‐benzyltetrahydroisoquinoline in which the signal of a 6‐methoxy group suffers a large upfield shift in the ^1^H NMR spectrum, whereas a 7‐methoxy group is relatively unaffected. This effect can be used to determine whether an RO‐substituent is in the 6‐ or 7‐position and, in particular, to distinguish isomeric derivatives with different RO‐groups in the 6‐ and 7‐positions. The method will allow the mechanism of cyclization of 3,4‐dimethoxybenzylaminoacetonitriles to be more fully elucidated.

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