Acrylic Acid → 3-(5-Fluoro-1H-indol-3-yl)propanoic acid

HRID 1461701Notes

Reaction equation

HRID 1461701 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[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:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:13][CH2:12][C:11]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 6581Acrylic AcidHCID 7918Acetic AnhydrideHCID 678615-Fluoroindole

Product 1

HCID 108997943-(5-Fluoro-1H-indol-3-yl)propanoic acidYield 57.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

Thus, a solution of 5-fluoroindole (1.35 g, 0.010 mole) in 10 mL of acetic acid containing acrylic acid (1.5 mL, 0.022 mole) and acetic anhydride (1.9 mL, 0.02 mole) was heated (oil bath) at 90° C. under Ar for 5 days. The volatiles were then removed in vacuo and the residue was taken up in 3 N NaOH. Insoluble material was removed by filtration and the filtrate was acidified with conc. HCl and then extracted with CH2Cl2. The organic extract was dried (Na2SO4) and evaporated to give the product (1.19 g, 57%) as a solid which was used without further purification: IR (neat) 3420, 1710 cm-1 ; 1Hnmr (200 MHz, CDCl3) δ 7.94 (br s, 1H), 7.28-7.18 (m, 3H), 7.05 (d, J=2.5 Hz, 1H), 6.93 (dt, J=9.0, 2.6 Hz, 1H), 3.05 (t, J=7.5 Hz, 2H), 2.73 (t, J=7.6 Hz, 2H).

Workup

  1. customThe volatiles were then removed in vacuo
  2. customInsoluble material was removed by filtration
  3. extractionextracted with CH2Cl2
  4. extractionThe organic extract
  5. dry with materialwas dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-e9556c422ba244768964d2d45c276d9b
Source dataset
uspto-grants-1991_12
Patent number
US05077293

Reaction notes

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