Pentamethylbenzene → 2-amino-N-(5-chloro-2-pyridinyl)-3-hydroxybenzamide

Participants

Reaction Conditions

Reaction Steps

To 7.44 g of 3-benzyloxy-N-(5-chloro-2-pyridyl)-2-nitrobenzamide were added 40 ml of trifluoroacetic acid and 3.72 g of pentamethylbenzene and the mixture was stirred at 40° C. for one night. The reaction solution was concentrated in vacuo, to the residue was added a saturated aqueous solution of sodium hydrogen carbonate to such an extent that the residue did not become alkaline and the mixture was extracted with chloroform. The organic layer was extracted with 1N aqueous solution of sodium hydroxide, the aqueous layer was made acidic by addition of hydrochloric acid thereto and the mixture was extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, the solvent was evaporated in vacuo and to the resulting residue were added 200 ml of suspension of Raney nickel in ethanol. This was stirred for 6 hours in a hydrogen atmosphere, N,N-dimethylformamide was added thereto and the insoluble matter was filtered off. The solvent was evaporated in vacuo and water was added to the resulting residue. The resulting precipitate was collected by filtration and dried in vacuo to give 4.58 g of 2-amino-N-(5-chloro-2-pyridyl)-3-hydroxybenzamide.

Provenance & Evidence