Phenylhydrazine → 1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-one
Reaction equation
C[N:2]([CH:4]=[C:5]1[C:10](=O)[CH2:9][CH2:8][CH2:7][C:6]1=[O:12])C.[C:13]1([NH:19]N)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO>[C:13]1([N:19]2[C:10]3[CH2:9][CH2:8][CH2:7][C:6](=[O:12])[C:5]=3[CH:4]=[N:2]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 2-((dimethylamino)methylene)cyclohexane-1,3-dione (14 g, 83 mmol) in methanol (150 mL) was added phenyl hydrazine (8.92 g, 83 mmol). The reaction mixture was refluxed for 6 hours. The reaction was then concentrated under reduced pressure followed by the addition of n-butanol (130 mL) and glacial acetic acid (2 mL). The reaction mixture was refluxed for 3 hours. On the completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was triturated with ether (100 mL) to give a precipitate, which was filtered and dried under reduced pressure to give the desired product (4.6 g, 30%) as a solid. 1H NMR (DMSO-d6, 400 MHz): δ 9.06 (s, 1H), 7.59-7.51 (m, 4H), 7.45-7.40 (m, 1H), 3.00 (t, J=6.4 Hz, 2H), 2.58 (t, J=6.4 Hz, 2H), 2.21 (quintet, J=6.4 Hz, 2H). LCMS [M+H]: 213.