Acrylic Acid → HCID 14501419, compound

HRID 1904663Notes

Reaction equation

HRID 1904663 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][CH2:11][C:12]([OH:14])=O)[CH:5]=[CH:6][C:7]=1[F:8].ClC1C=C(C=CC=1F)N.C(O)(=O)C=C.C(OC)(=O)C=C>ClCCl.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:12](=[O:14])[CH2:11][CH2:10][NH:9]2)=[CH:6][C:7]=1[F:8]

Participants

7

Reactant 4

HCID 6581Acrylic AcidHCID 7294Methyl AcrylateHCID 97083-Chloro-4-fluoroanilineHCID 15020409HCID 15020409, compound

Product 1

HCID 14501419HCID 14501419, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of polyphosphoric acid (600 g) and 3-(3-chloro-4-fluorophenylamino)propionic acid (38 g), which was synthesized from 3-chloro-4-fluoroaniline and acrylic acid or methyl acrylate by the method of W.S. Johnson et al. (The Journal of American Chemical Society, volume 71, page 1901, (1949)), was stirred at 110° C. for 70 minutes. The reaction mixture was poured into 1500 ml of water, then shaken with dichloromethane (1500 ml). The organic layer was washed twice with saturated agqueous NaCl solution (200 ml each) and dried over anhydrous sodium sulfate. Dichloromethane was removed in vacuo and the residue was subjected to silica gel colum chromatography using a mixed solvent (n-hexane: ether-4:1) to obtain 7-chloro-6-fluoro-2,3-dihydro-4(1H)-quinolinone (yield 20 g) as pale yellow crystal.

Workup

  1. washThe organic layer was washed twice with saturated agqueous NaCl solution (200 ml each)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customDichloromethane was removed in vacuo

Sources & evidence

ORD record
ord-801b3c95e2944fb5af879512c9ef9ecd
Source dataset
uspto-grants-1989_06
Patent number
US04839368

Reaction notes

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