Dimethylformamide → 2-Methoxy-6-(4-methoxyphenyl)-1-napthonitrile

HRID 895183Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:20][CH3:21].[C:22]([Cu])#[N:23].CN(C=O)C>C(OCC)(=O)C>[CH3:21][O:20][C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[C:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[CH:7]=2)[C:2]=1[C:22]#[N:23]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1-bromo-2-methoxy-6-(4-methoxyphenyl)naphthalene (0.76 g, 2.21 g), CuCN (0.24 g, 2.66 mmol) and DMF (10 mL) was stirred at 120° C. for 4 hr. The reaction mixture was cooled to room temperature, slurried with ethyl acetate, filtered through silica, and evaporation of the solvent, and purification by silica column chromatography (20% ethyl acetate—hexanes) yielded 0.19 g (30%) of the title compound as a pale yellow solid: mp 182-185° C.; 1H NMR (CDCl3): δ 3.88 (3H, s), 4.09 (3H, s), 7.03 (2H, d, J=8.73 Hz), 7.29 (1H, d, J=9.12 Hz), 7.63 (2H, d, J=8.73 Hz), 7.88 (1H, dd, J=1.98 Hz, J=8.73 Hz), 7.97 (1H, d, J=1.98 Hz), 8.09 (1H, d, J=9.12 Hz), 8.14 (1H, d, J=8.73 Hz).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered through silica, and evaporation of the solvent, and purification by silica column chromatography (20% ethyl acetate—hexanes)

Sources & evidence

ORD record: ord-c6bcbccac43d4d6c8eef8c6a6c4b27bf
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06914074B2

Reaction notes

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