Potassium Carbonate → HCID 178515185, compound

HRID 341061

Reaction equation

HRID 341061 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=[C:3]1[C:12]([O:14]CC)=O.P(Cl)(Cl)(Cl)=O.[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH:29][NH2:30].C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[F:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]1[C:12](=[O:14])[C:3]2=[CH:4][NH:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:2]2=[N:30]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 220876Ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylateHCID 4238442-Fluorophenylhydrazine hydrochloride

Product 1

HCID 178515185HCID 178515185, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate (3.8 g, 17 mmol) was dissolved in phosphorus oxychloride (25 mL, 0.26 mol, 15 equiv) and stirred at ambient temperature for 14 hours. The mixture was concentrated in vacuo and the residue was concentrated from toluene (3×25 mL). The resulting residue was dissolved in 1,2-dimethoxyethane (60 mL) and degassed N,N-dimethylformamide (10 mL) and treated with 2-fluorophenylhydrazine (4.4 g, 35 mmol, 2 equiv) and potassium carbonate (12 g, 87 mmol, 5 equiv). The mixture was placed into a preheated oil bath at 80° C. for 14 hours. The mixture was cooled to ambient temperature, diluted with water (100 mL) and ethyl acetate (100 mL) and filtered. The solid was collected and dried in vacuo, providing the titled compound as a yellow solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. concentrationthe residue was concentrated from toluene (3×25 mL)
  3. dissolutionThe resulting residue was dissolved in 1,2-dimethoxyethane (60 mL)
  4. customdegassed N,N-dimethylformamide (10 mL)
  5. waitThe mixture was placed into a preheated oil bath at 80° C. for 14 hours
  6. temperatureThe mixture was cooled to ambient temperature
  7. filtrationfiltered
  8. customThe solid was collected
  9. customdried in vacuo

Sources & evidence

ORD record
ord-2fb7e142bd944a25baabe0eeeb5d94ca
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Linked notes

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