Sulfuric Acid → HCID 86749416, compound

HRID 2295204Notes

Reaction equation

HRID 2295204 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH:9]([CH3:11])[CH3:10].[F:13][C:14]1[CH:27]=[CH:26][C:17]([C:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=O)=[CH:16][CH:15]=1.OS(O)(=O)=O.[NH4+].[OH-]>CC(O)=O.O.CCCCCC.CCOC(C)=O>[F:13][C:14]1[CH:27]=[CH:26][C:17]([C:18]2[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:8]([CH:9]([CH3:11])[CH3:10])[C:3]3[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=3)[N:1]=2)=[CH:16][CH:15]=1

Participants

9

Reactant 4

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 2758844Ethyl 3-(4-Fluorophenyl)-3-OxopropanoateHCID 122976071-(2-aminophenyl)-2-methylpropan-1-one

Product 1

HCID 86749416HCID 86749416, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(2-aminophenyl)-2-methyl-1-propanone (5.526 gm, 33.9 mmol), ethyl p-fluorobenzoylacetate (7.12 gm, 33.9 mmol) and concentrated H2SO4 (0.34 ml) in glacial HOAc (34 ml) was refluxed for 22 hours. The reaction mixture was cooled to room temperature and poured into an ice-cold solution of concentrated NH4OH (48 ml) in H2O (120 ml). The resulting mixture was extracted twice with Et2O and the combined Et2O layers were washed with H2O and brine, then dried (Na2SO4), filtered and stripped to yield a cloudy brown oil. Flash chromatography (Merck SiO2, 10% EtOAc in hexane) afforded impure 2-(4-fluorophenyl)-4-(1-methylethyl)-3-quinoline-carboxylic acid, ethyl ester as an oil. Most of the volatile impurities were distilled off under an oil pump vacuum (bath temp. 85° C.), leaving a yellow oil (5.096 gm) which was 77% by weight 2-(4-fluorophenyl)-4-(1-methylethyl)-3-quinolinecarboxylic acid, ethyl ester (34% effective yield).

Workup

  1. temperaturewas refluxed for 22 hours
  2. extractionThe resulting mixture was extracted twice with Et2O
  3. washthe combined Et2O layers were washed with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customto yield a cloudy brown oil

Sources & evidence

ORD record
ord-83b60ebc60944c6ab7f66a8756a841e3
Source dataset
uspto-grants-1997_11
Patent number
US05691322

Reaction notes

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