Hydrochloric Acid → N-Nitrosodiphenylamine

Reaction equation

[C:1]1([N:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N([O-])=[O:16].[Na+].Cl>CN(C)C=O>[N:8]([N:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:16]

Participants

Procedure

The compound 1,1-diphenylhydrazine is commercially available. The substituted 1,1-diphenylhydrazines can be made by reacting the corresponding 1,1-diarylamine with sodium nitrite and hydrochloric acid in dimethylformamide at about 10° C. to produce an N-nitrosodiphenylamine, then adding the N-nitroso compound in tetrahydrofuran to a suspension of lithium aluminum hydride in dry ether under nitrogen and maintaining the temperature at 25°-35° C. for about 11/2 hours. The procedure is analogous to that given for preparation of N-amino-iminodibenzyl in Cohen et al., U.S. Pat. No. 3,457,271.