3-Chlorobutanoyl chloride → 1,2,3,4-Tetrahydro-6-nitrobenzofuro[3,2-c]-pyridine

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Reaction Conditions

Reaction Steps

1,2,3,4-tetrahydro-2-methyl-6-nitrobenzofuro[3,2-c]pyridine (0.0224 mol), prepared according to the procedure described in J. Chem. Soc. (C), 1971, p53-60, was dissolved in 1,2-dichloroethane (40 ml), and cooled to 0° C. At this temperature, (1-chloroethyl) acetylchloride (0.0291 mol) was added dropwise. The suspension was stirred and refluxed for 2 hours. 1,2-dichloroethane was evaporated. The mixture was dissolved in methanol, stirred and refluxed for 2 hours, then filtered. Both the filtrate and crystals were treated with 2 N Na2CO3 and this mixture was extracted with CH2Cl2. The separated organic layer was dried, filtered, and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 90/10). The desired fractions were collected and the solvent was evaporated, yielding 1.5 g 1,2,3,4-tetrahydro-6-nitrobenzofuro[3,2-c]-pyridine (intern. 4).

Provenance & Evidence