Chloroform → N-Phenyl-1,2,3,4-tetrahydronaphthalen-2-amine

Participants

Reaction Conditions

Reaction Steps

2.37 grams (0.01 mol.) of 2-phenylaminotetralone (formula I: R = phenyl) are refluxed during 6 hours in 50 ml of ethanol, in the presence of one equivalent of tosylhydrazine. After the removal of the alcohol, 100 ml of alcohol-free chloroform are added to the residue (crude tosylhydrazone). After cooling to -10°C, 0.011 mol. of catecholborane are added and the reaction is allowed to take place during 30 minutes. 0.03 mol. of trihydrated sodium acetate are then added so as to initiate the decompositon of the intermediate addition product and the mixture is refluxed during 1 hour. After cooling, 100 ml of water are added and the pH is adjusted at 13. The obtained 2-phenylaminotetraline (yield: 80%) is extracted by means of chloroform and converted into hydrochloride. Melting point: 193° - 196°C.

Provenance & Evidence