Ethanol → HCID 54112706, compound

HRID 398030Notes

Reaction equation

HRID 398030 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[CH:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1.[CH2:24](O)[CH3:25]>>[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[CH:17][C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)[C:14]([O:16][CH2:24][CH3:25])=[O:15])=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 54287785HCID 54287785, compound

Product 1

HCID 54112706HCID 54112706, compound

Procedure

Conc. sulfuric acid (2.2 ml) was added carefully to a suspension of 2-(4-fluorophenyl)-3-(4-pyridyl)-acrylic acid (6.7 g, 27.5 mmol) in ethanol (120 ml) and the mixture was heated at reflux for 24 h. The solvent was evaporated, the remainder was taken up in dichloromethane and the organic solution was washed with aqueous sodium hydrogencarbonate and water, followed by drying and evaporation. Flash column chromatography on silica gel (hexane-acetone=2:1) provided the pure title compound. MS (m/z): 271.8 (M+H)+; C16H14FNO2 requir. 271.3 1H-NMR (CDCl3): 8.44, 6.88 (2 m, each 2H, Pyrid.), 7.72 (s, 1H, CH═), 7.16, 7.06 (2 m, each 2H, PhF), 4.28 (q, 2H, CH2), 1.28 (t, 3H, CH3).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 24 h
  3. customThe solvent was evaporated
  4. washthe organic solution was washed with aqueous sodium hydrogencarbonate and water
  5. customby drying
  6. customevaporation

Sources & evidence

ORD record
ord-628a9f55aaf54df5b99884bfde174e20
Source dataset
uspto-grants-2003_08
Patent number
US06610698B2

Reaction notes

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