Ethanol → 2-Thiophen-2-yl-quinoline-4-carboxylic acid

HRID 2394809Notes

Reaction equation

HRID 2394809 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[C:12]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)(=O)[CH3:13].[OH-].[K+].CC[OH:24]>O>[S:16]1[CH:17]=[CH:18][CH:19]=[C:15]1[C:12]1[CH:13]=[C:4]([C:2]([OH:24])=[O:3])[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:1]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 69202-AcetylthiopheneHCID 7054IsatinHCID 14797Potassium Hydroxide

Product 1

HCID 6204522-Thiophen-2-yl-quinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5 g (34.0 mmol) of isatin, 4.4 ml (40.8 mmol) of 2-acetylthiophene and 6.3 g (112.2 mmol) of potassium hydroxide were dissolved in 40 ml of abs. EtOH and the slurry heated at 80° C. for 16 hours. After cooling of the reaction mixture, 50 ml of water were added and the solution extracted with 50 ml of Et2O. The ice-cooled aqueous phase was acidified to pH 1 with 37% HCl and the precipitate collected by filtration and washed with water. The crude product obtained was dried in-vacuo at 40° C. and triturated with EtOAc to yield 4.8 g of the title compound.

Workup

  1. additionwere added
  2. extractionthe solution extracted with 50 ml of Et2O
  3. temperatureThe ice-cooled aqueous phase
  4. filtrationthe precipitate collected by filtration
  5. washwashed with water
  6. customThe crude product obtained
  7. customwas dried in-vacuo at 40° C.
  8. customtriturated with EtOAc

Sources & evidence

ORD record
ord-a3c306ef67de41bb96e0410e99db5cd2
Source dataset
uspto-grants-1998_09
Patent number
US05811553

Reaction notes

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