Hydrogen chloride-ethyl acetate → 10-Azatricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-4-yl cyanide Hydrochloride

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Reaction Steps

4-Cyano-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-triene-10-carboxylic acid tert-butyl ester was treated with 3N HCl ethyl acetate (6 mL) and warmed to reflux for 2 hours, then concentrated, dissolved in a minimum of methanol which was saturated with Et2O and stirred 18 hours. The product was collected by filtration (49 mg, 73%). 1H NMR (400 MHz, DMSO-d6)9.66 (br s, NH), 7.86 (br s, NH), 7.74–7.70 (m, 2H), 7.49 (d, J=7.5 Hz, 1H), 3.33–2.97 (m, 6H), 2.17 (m, 1H), 2.01 (d, J=11.0 Hz, 1H). GCMS m/e 184 (M+). M.p. 268–273° C.

Provenance & Evidence