3-[5-Hydroxy-2-(4-hydroxyphenyl)-benzofuran-7-yl]-acrylamide → 3-[5-Hydroxy-2-(4-hydroxy-phenyl)-benzofuran-7-yl]-acrylonitrile

HRID 1794500Notes

Reaction equation

HRID 1794500 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]([NH2:22])=O)[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)=[CH:7][C:6]=2[CH:17]=1>CN(C=O)C.P(Cl)(Cl)(Cl)=O>[OH:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]#[N:22])[C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=3)=[CH:7][C:6]=2[CH:17]=1

Participants

4

Reactant 1

HCID 688451963-[5-Hydroxy-2-(4-hydroxyphenyl)-benzofuran-7-yl]-acrylamide

Product 1

HCID 688406933-[5-Hydroxy-2-(4-hydroxy-phenyl)-benzofuran-7-yl]-acrylonitrileYield 10.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 24813Phosphorus oxychlorideSolvent

Procedure

A solution of 3-[5-hydroxy-2-(4-hydroxyphenyl)-benzofuran-7-yl]-acrylamide 61 (0.07 g, 0.24 mmol) in DMF (5 mL) and phosphorous oxychloride (0.11 mL) was heated at 65° C. for 2 hours. Then ice was added to the reaction mixture and the product extracted into ethyl acetate. The organic layer was dried over MgSO4 and the solvent removed in vacuo. The crude product was submitted for reverse phase prep HPLC. The product was isolated to give 0.007 g of 3-[5-hydroxy-2-(4-hydroxy-phenyl)-benzofuran-7-yl]-acrylonitrile 64: 1H NMR (DMSO-d6) δ 9.90 (s, 1 H), 9.48 (s, 1 H), 7.82 (d, 2 H, J=8.6 Hz), 7.79 (d, 1 H, J=16.7 Hz), 7.13 (s, 1 H), 7.03 (d, 1 H, J=2.3 Hz), 6.92 (d, 1 H, J=2.4 Hz), 6.88 (d, 2 H, J=8.7 Hz), 6.71 (d, 1 H, J=16.8 Hz); MS 276 (M−H)−.

Workup

  1. additionThen ice was added to the reaction mixture
  2. extractionthe product extracted into ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent removed in vacuo
  5. customThe product was isolated

Sources & evidence

ORD record
ord-98b2bf75882f4df1bba4954ec7561d0c
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

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