Triethylamine → Ethyl 6,7-difluoroquinoline-3-carboxylate

HRID 413047Notes

Reaction equation

HRID 413047 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[C:9]([F:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(N(CC)CC)C>C(O)C.[Pd]>[F:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[F:13])[N:5]=[CH:4][C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:2]2

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 1511944Ethyl 4-chloro-6,7-difluoroquinoline-3-carboxylate

Product 1

HCID 18523329Ethyl 6,7-difluoroquinoline-3-carboxylateYield 92.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 52.9 g of ethyl 4-chloro-6,7-difluoroquinoline-3-carboxylate in 750 cm3 of ethanol, in the presence of 19.7 g of triethylamine, was hydrogenated at atmospheric pressure, at a temperature in the region of 20° C., for 1 hour in the presence of 3 g of 5% palladium on carbon (type D). After removing the catalyst by filtration at high temperature, being concentrated to dryness under reduced pressure (5.2 kPa) at about 50° C., the residue was taken up, with stirring, in 1.2 liters of water, dewatered, and washed 3 times with 200 cm3 of water. It was dissolved in 1 liter of diethyl ether; the ethereal extracts were washed twice with 100 cm3 of water and were dried over sodium sulphate. After filtration and concentration under reduced pressure (5.2 kPa), the compound obtained was recrystallized from 600 cm3 of diisopropyl ether. 42.8 g of ethyl 6,7-difluoroquinoline-3-carboxylate was obtained in the form of white crystals, which melted at 135° C.

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration at high temperature
  3. concentrationbeing concentrated to dryness under reduced pressure (5.2 kPa) at about 50° C.
  4. washwashed 3 times with 200 cm3 of water
  5. dissolutionIt was dissolved in 1 liter of diethyl ether
  6. washthe ethereal extracts were washed twice with 100 cm3 of water
  7. dry with materialwere dried over sodium sulphate
  8. filtrationAfter filtration and concentration under reduced pressure (5.2 kPa)
  9. customthe compound obtained
  10. customwas recrystallized from 600 cm3 of diisopropyl ether

Sources & evidence

ORD record
ord-ee41f2bfa8334ffe88597ef826a25796
Source dataset
uspto-grants-2003_05
Patent number
US06566362B2

Reaction notes

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