Ethanol → HCID 54112706, compound

HRID 2188464Notes

Reaction equation

HRID 2188464 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)+; C16H14FNO2requir. 271.3 1H-NMR (CDCl3): 8.44, 6.88 (2m, each 2H, Pyrid.), 7.72 (s, 1H, CH═), 7.16, 7.06 (2m, 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-9994c62bea8d4714890da4d49203aca4
Source dataset
uspto-grants-2002_06
Patent number
US06410729B1

Reaction notes

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