2-Methylcyclohexanone → HCID 12050052, compound

HRID 2308237Notes

Reaction equation

Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[CH3:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1=O>>[Br:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][CH:17]1[C:12]2([CH3:11])[CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

Reactant 2

HCID 114192-Methylcyclohexanone

HCID 121574-Bromophenylhydrazine hydrochloride

Product 1

HCID 12050052HCID 12050052, compoundYield 65%

Procedure

This compound was prepared by the procedure of Example 1 using 4-bromo-phenyl hydrazine hydrochloride (2.0 g, 8.95 nmmol) and 2-methylcyclohexanone (1.0 g, 8.95 mmol). The subtitled compound (1.5 g, 65%) was obtained as ayellow oil: 1H NMR (CDCl3) δ 1.26 (s, 3H), 1.38-1.46 (rn, 4H), 1.56-1.68 (m, 4H), 3.4 (t, J=4.4 Hz, 1H), 3.6 (br s, 1H), 6.53 (d, J=8 Hz, 1H), 7.08 (d, J=2.0 Hz, 1H), 7.09 (dd, J=8.0, 2.0 Hz, 1H); 13C-NMR (CDCl3) δ 21.45, 21.87 (t), 23.96 (q), 27.92, 35.32 (t), 43.56 (s), 66.65 (d), 110.73 (s), 111.88, 125.25, 129.99 (d), 142.17, 149.03 (s), MS (EI) m/z 268, 270 (M+H)+.

Sources & evidence

ORD record: ord-7470b93a07db4ca29734b86dc88cbf6d
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06835744B2

Reaction notes

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