N-(2-Fluorophenyl) cinnamamide → 8-Fluoroquinolin-2(1H)-one

HRID 75348Notes

Reaction equation

HRID 75348 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:18])[CH:10]=[CH:11]C1C=CC=CC=1.[Cl-].[Cl-].[Cl-].[Al+3]>ClC1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[NH:8][C:9](=[O:18])[CH:10]=[CH:11]2

Participants

4

Reactant 2

HCID 303250N-(2-Fluorophenyl) cinnamamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 198986748-Fluoroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
125 °C

Procedure

N-(2-Fluorophenyl)cinnamamide (10.5 g, 44 mmol) was dissolved in chloro-benzene (60 mL) and aluminum trichloride (29.0 g, 218 mmol, 5 eq) was added. The reaction was heated to 125° C. for 3 h and then cooled to rt over 45 min. The reaction was poured onto 300 g of ice with stirring, producing a tan solid. The solid was filtered and washed with 100 mL of water and 3×100 mL of hexanes and dried under high vacuum. The solid was extracted with 1 L of DCM and filtered to remove insoluble byproducts. The solvent was removed in vacuo to afford 8-fluoroquinolin-2(1H)-one. 1H NMR (400 MHz, CDCl3) δ ppm 10.95 (br s, 1H), 7.77 (dd, J=9.8, 1.6 Hz, 1H), 7.35 (d, J=7.8 Hz, 1H), 7.27 (ddd, J=10.2, 7.8, 1.2 Hz, 1H), 7.14 (td, J=8.0, 5.1 Hz, 1H), 6.76 (d, J=9.4 Hz, 1H).

Workup

  1. temperaturecooled to rt over 45 min
  2. customproducing a tan solid
  3. filtrationThe solid was filtered
  4. washwashed with 100 mL of water and 3×100 mL of hexanes
  5. customdried under high vacuum
  6. extractionThe solid was extracted with 1 L of DCM
  7. filtrationfiltered
  8. customto remove insoluble byproducts
  9. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-af76ff157f9445a5b2d640c5f613b844
Source dataset
uspto-grants-2014_09
Patent number
US08835432B2

Reaction notes

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