Acrylic Acid → 3-(6-Fluoroindolyl)propionic acid

HRID 1764891Notes

Reaction equation

HRID 1764891 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[C:11]([OH:15])(=[O:14])[CH:12]=[CH2:13].C(OC(=O)C)(=O)C>C(O)(=O)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH2:13][CH2:12][C:11]([OH:15])=[O:14])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6581Acrylic AcidHCID 7918Acetic AnhydrideHCID 3512786-Fluoroindole

Product 1

HCID 227354403-(6-Fluoroindolyl)propionic acidYield 52.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
20 °C

Procedure

The solution of 6-fluoroindol (300 mg, 2.22 mmol), acrylic acid (352 mg, 4.88 mmol) and acetic anhydride (453 mg, 4.44 mmol) in acetic acid (1.1 mL) was heated at 90° C. for 15 h. The reaction mixture was cooled to 20° C. then concentrated in vacuo. The residue was dissolved in 3N NaOH. The solution was filtered to remove insoluble material and the filtrate was acidified with conc. HCl and extracted with CHCl3. The organic solution was dried over MgSO4, filtered and concentrated in vacuo to give 3-(6-fluoroindolyl)propionic acid (240 mg, 52%) as a yellow solid.

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue was dissolved in 3N NaOH
  3. filtrationThe solution was filtered
  4. customto remove insoluble material
  5. extractionextracted with CHCl3
  6. dry with materialThe organic solution was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b9c5b47635cd42658b044e8ac26a8659
Source dataset
uspto-grants-2007_06
Patent number
USRE039679E1

Reaction notes

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