6-Chloro-8-nitroquinoline → 6-Chloro-8-aminoquinoline

Participants

Reaction Steps

To a hot suspension of 6-chloro-8-nitroquinoline (Mosher, et al., Org. Syn. 27:48 (1947), 0.8 g) in a mixture of ethanol/glacial acetic acid/water (2:2:1, 25 mL) was added iron powder (0.5 g) portionwise. The resulting mixture was stirred at reflux for 1.5 hours. The reaction was the cooled to room temperature, filtered through celite and made basic by addition of solid Na2CO3. The aqueous mixture was extracted with Et2O. The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated on a rotary evaporator to give the desired product (0.5 g) as a yellow solid; MP. 70-73° C.; MS (ES) m/z (relative intensity) 179 (M+H)+ (100).

Provenance & Evidence