Hydrochloric Acid → 1-benzoyl-5-chloromethyl-2,3-dihydro-1H-indole

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Reaction Steps

1-Benzoyl-2,3-dihydro-1H-indole (Beilstein, 20, 275) (5.58 g, 25 mmole) is dissolved in 50 ml of glacial acetic acid, then 56 ml (ca 70 mmoles) of 40% formaldehyde are added, and dry hydrogen chloride passed into the solution which is maintained at 70° for 3 hours. The solution is evaporated, and the residue dissolved in benzene, and again evaporated to dryness to give 6.53 g of crude product. This residue is treated with carbon tetrachloride-hexane to give 4.05 g (60%) of 1-benzoyl-5-chloromethyl-2,3-dihydro-1H-indole, m.p. 107.5°-110.0°.

Provenance & Evidence