Dimethylformamide → 7-Methoxynaphthalene-1-carbonitrile

HRID 895221Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[NH4+].[Cl-].[CH3:16][N:17](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[CH:4][CH:3]=[C:2]2[C:16]#[N:17])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1-bromo-7-methoxy-naphthalene (3.26 g, 13.8 mmol), Zn(CN)2 (2.26 g, 19.2 mmol), and tetrakis(triphenylphosphine)palladium (1.6 g, 1.4 mmol) in DMF (50 mL) was stirred at 120° C. for 15 hr. The cooled reaction mixture was poured into 200 mL 1 N NH4Cl solution and extracted with ethyl acetate (3×350 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, evaporation of the solvent, and purification on a silica column (10% ethyl acetate—hexanes) yielded 1.28 g (51%) of the title compound as a white solid: mp 62-66° C.; 1H NMR (DMSO-d6): δ 4.00 (3H, s), 7.25 (1H, dd, J=2.48 Hz, J=8.96 Hz), 7.36-7.47 (1H, m), 7.47 (1H, d, J=2.39 Hz), 7.81 (1H, d, J=9.00 Hz), 7.88 (1H, dd, J=0.81 Hz, J=7.23 Hz), 8.00 (1H, d, J=8.21 Hz); MS (EI) m/z 183 (M)+;

Workup

customThe cooled reaction mixture
extractionextracted with ethyl acetate (3×350 mL)
washThe combined organic layers were washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporation of the solvent, and purification on a silica column (10% ethyl acetate—hexanes)

Sources & evidence

ORD record: ord-22faa7f60a984383bd8f7e58201f054a
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06914074B2

Reaction notes

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