Sodium Sulfate → 2-Methyl-1,2,3,4-tetrahydrobenzo[g]isoquinolin-5-amine

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Reaction Steps

A solution of 50.0 g of 5-amino-1,2,3,4-tetrahydrobenzo[g]isoquinolin-2-ylcarboxylic acid ethyl ester (see Example 4a-c for production) in 1.2 litres of anhydrous tetrahydrofuran is added dropwise at temperatures of between 15° - 30° to a suspension of 23.0 g of lithium aluminium hydride in 500 ml of anhydrous tetrahydrofuran while cooling. The reaction mixture is stirred for 5 hours at the boiling temperature, is cooled to 0° and is decomposed by the dropwise addition of 90 ml of a saturated sodium sulphate solution at 0° - 5°. The precipitated inorganic product is filtered off, is washed with tetrahydrofuran and concentrated by evaporation. The title compound crystallizes from the evaporation residue with the addition of ethanol and is again recrystallized from ethanol. M.Pt.: 97° - 99°.

Provenance & Evidence