4-Chlorophenol → HCID 58168060, compound

HRID 1029096Notes

Reaction equation

HRID 1029096 reaction equation
F[C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.[Cl:17][C:18]1[CH:23]=C[C:21](O)=[CH:20][CH:19]=1.[C:25](=[O:28])([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:17][C:18]1[CH:23]=[C:25]([CH:21]=[CH:20][CH:19]=1)[O:28][C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 58168117HCID 58168117, compound

Product 1

HCID 58168060HCID 58168060, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
180 °C

Procedure

9-Fluoro-5H-benzo[c][1,8]naphthyridin-6-one (40 mg, 0.19 mmol), 4-chlorophenol (72 mg, 0.56 mmol), and potassium carbonate (129 mg, 0.93 mmol) were suspended in DMF (1.5 mL), and stirred for 20 minutes at 180° C. in the microwave. The reaction mixture was quenched with H2O. The resulting precipitate was filtered, washed with H2O, and dried under vacuum to provide 74 (59 mg, 98% yield) as a tan solid. LC-MS (M+H=323, obsd.=323). 1H NMR (400 MHz, d6-DMSO): δ 12.02 (s, 1H), 8.77 (dd, 1H), 8.51 (dd, 1H), 8.33 (d, 1H), 8.15 (d, 1H), 7.52 (m, 2H), 7.23 (m, 4H).

Workup

  1. customThe reaction mixture was quenched with H2O
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with H2O
  4. customdried under vacuum

Sources & evidence

ORD record
ord-6e2e5bc528da4745b2d419c1acd331e3
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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