1,2-Dichloroethane → 2-Quinolinecarboxylic acid, pentafluorophenyl ester

HRID 862974Notes

Reaction equation

HRID 862974 reaction equation
[C:1]([OH:13])(=[O:12])[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[F:14][C:15]1[C:20](O)=[C:19]([F:22])[C:18]([F:23])=[C:17]([F:24])[C:16]=1[F:25].C1COCC1.C(Cl)CCl>C(OCC)C.CCCCCC>[F:14][C:15]1[C:20]([O:12][C:1](=[O:13])[C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)=[C:19]([F:22])[C:18]([F:23])=[C:17]([F:24])[C:16]=1[F:25]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 7124Quinaldic AcidHCID 8028TetrahydrofuranHCID 13041Pentafluorophenol

Product 1

HCID 109258152-Quinolinecarboxylic acid, pentafluorophenyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

An oven dried single necked round bottom flask was charged with 15.0 g quinaldic acid (86.6 mmol), 20.8 g pentafluorophenol (113 mmol), and 200 mL THF. The suspension was stirred, and 18.3 g EDC (95.3 mmol) was added in one portion. Vigorous stirring was continued at room temperature for two hours, during which time a gummy precipitate formed at the bottom of the flask. The solution was decanted from the gum, and the gum was washed with CH2C12. The combined organic layers were diluted with hexane and washed once with 50 mL 0.1N NaHSO4, twice with 50 mL 1N K2CO3, and once with 50 mL brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo, affording a pale pink solid. The solid was dissolved in 30 mL hot diethyl ether and 400 mL hot hexane was added. The solution was allowed to cool to room temperature, and then to 0° C. over a period af 1.5 hours. The desired product was collected as colorless needles (21.6 g, 73%) by filtration.

Workup

  1. customAn oven dried single necked round bottom flask
  2. stirringVigorous stirring
  3. customa gummy precipitate formed at the bottom of the flask
  4. customThe solution was decanted from the gum
  5. washthe gum was washed with CH2C12
  6. additionThe combined organic layers were diluted with hexane
  7. washwashed once with 50 mL 0.1N NaHSO4, twice with 50 mL 1N K2CO3
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customaffording a pale pink solid
  12. waitto 0° C. over a period af 1.5 hours
  13. filtrationThe desired product was collected as colorless needles (21.6 g, 73%) by filtration

Sources & evidence

ORD record
ord-ea038beaec4e4a299db1e7d899211681
Source dataset
uspto-grants-1998_02
Patent number
US05719287

Reaction notes

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