Potassium Carbonate → HCID 21864973, compound

HRID 856954Notes

Reaction equation

HRID 856954 reaction equation
[OH:1][C:2]1[C:3]([C:12]#[N:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.O>[NH2:13][C:12]1[C:3]2[CH:4]=[C:5]3[C:10]([CH:9]=[CH:8][CH:7]=[CH:6]3)=[CH:11][C:2]=2[O:1][C:15]=1[C:16]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])=[O:17]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 202502,2',4'-TrichloroacetophenoneHCID 129902643-Hydroxynaphthalene-2-carbonitrile

Product 1

HCID 21864973HCID 21864973, compoundYield 57.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 3-hydroxy-naphthalene-2-carbonitrile from step 2 (200 mg, 1.18 mmol) and 2,2′,4′-trichloroacetophenone (317 mg, 1.42 mmol, 1.2 eq) in anhydrous N,N-dimethylformamide (4.7 mL) was added potassium carbonate (326.7 mg, 2.36 mmol, 2.0 eq), and the orange reaction mixture was stirred at 80° C. for 16 h. The resulting dark wine colored reaction was diluted with ethyl acetate and water. The organic layer was washed with saturated aqueous ammonium chloride, water, brine, and dried over magnesium sulfate. The solvent was removed at reduced pressure and the crude product was purified on the MPLC (biotage) eluted with 15% ethyl acetate-hexane. Crystallization from ether-hexane afforded 243 mg (57.7%) of the desired benzofuran. 1H-NMR (DMSO-d6) δ 8.66 (s, 1H), 7.99 (d, J=8.1 Hz, 1H), 7.93 (d, J=8.1 Hz, 1H), 7.88 (s, 1H), 7.76 (d, J=1.5 Hz, 1H), 7.72 (broad s, 2H), 7.63 to 7.42 (m, 4H); LC-MS (ES MH+=356).

Workup

  1. customThe resulting dark wine colored reaction
  2. washThe organic layer was washed with saturated aqueous ammonium chloride, water, brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed at reduced pressure
  5. customthe crude product was purified on the MPLC (biotage)
  6. washeluted with 15% ethyl acetate-hexane
  7. customCrystallization from ether-hexane

Sources & evidence

ORD record
ord-51767a93a7d6407a989ec9f10d456abe
Source dataset
uspto-grants-2006_12
Patent number
US07144885B2

Reaction notes

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