Hexane → Benzenamine, 3-methoxy-N-(4-methylphenyl)-

HRID 1598971Notes

Reaction equation

[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8].I[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1.CCCCCC>CN(C)P(N(C)C)(N(C)C)=O.[Cu]I>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:5]([O:4][CH3:3])[CH:6]=2)=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To a suspension of 0.11 g (4.6 mmol, hexane washed 3 x, 50-60% in oil) sodium hydride in 1.0 mL of hexamethylphosphoramide was cannulated a solution of 0.11 g (0.89 mmol) of 3-methoxyaniline in 2.0 mL hexamethylphosphoramide. The resulting mixture was heated at 55° C. for 20 min. To this was added 0.18 g (0.93 mmol) of copper(I) iodide and the mixture was heated at 55° C. for 1.5 hours. 4-iodotoluene was added and the reaction heated at 85° C. for 3 hours. The reaction mixture was allowed to cool to room temperature, hexane was added and the reaction was then loaded onto a silica gel column. The mixture was purified by flash chromatography (100% hexane, 5% ethyl acetate in hexanes) to give the title compound as an orange oil. PNMR (300 MHz, CDCl3) d 2.30 (3 H, s), 3.76 (3 H, s), 5.65 (1 H, s), 6.43 (1 H, m), 6.57 (1 H, d, J=1.6 Hz), 6.58 (1 H, m), 7.01 (2 H, d, J=8.5 Hz), 7.09 (2 H, d, J=8.5 Hz), 7.15 (1 H, d, J=8.6 Hz).

Workup

temperaturethe mixture was heated at 55° C. for 1.5 hours
temperaturethe reaction heated at 85° C. for 3 hours
temperatureto cool to room temperature
customThe mixture was purified by flash chromatography (100% hexane, 5% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-39528a2fb1c14057951fb8463a4257f5
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739338

Reaction notes

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