Cesium carbonate → 6-(2,2-Dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline

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Reaction Steps

6-Hydroxy-1-oxo-1,2,3,4-tetrahydroisoquinoline is treated with bromoacetaldehyde dimethyl acetal, in the presence of Cs2CO3 and CsI in DMF to yield 6-(2,2-dimethoxyethoxy)- 1-oxo-1,2,3,4-tetrahydroisoquinoline. Treatment with 2-chloromethylpyridine hydrochloride in the presence of sodium hydride in DMF yields 6-(2,2-dimethoxyethoxy) 2-(2-pyridylmethyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline. Hydrolysis with 20% aqueous sulfuric acid in THF yields α-[2-(2-pyridylmethyl)-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yloxy]-acetaldehyde which is then converted to 2-(2-pyridylmethyl)-6-[2-(N-hydroxyamino)-ethoxy]-1-oxo-1,2,3,4-tetrahydroisoquinoline.

Provenance & Evidence