Potassium tert-butoxide → Ethyl 1-cyclohexyl-7-iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylate

HRID 963402Notes

Reaction equation

HRID 963402 reaction equation
Cl[C:2]1[CH:23]=[C:22]([I:24])[CH:21]=[CH:20][C:3]=1[C:4]([C:6](=[CH:12][NH:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].CC([O-])(C)C.[K+]>CS(C)=O>[CH:14]1([N:13]2[C:20]3[C:3](=[CH:2][CH:23]=[C:22]([I:24])[CH:21]=3)[C:4](=[O:5])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 178471915HCID 178471915, compound

Product 1

HCID 19081790Ethyl 1-cyclohexyl-7-iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylateYield 90.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

mg) A suspension of 17.8 g of ethyl 2-(2-chloro-4-iodo-benzoyl)-3-cyclohexylamino-acrylate in 150 ml of dimethyl sulphoxide is treated portionwise at room temperature while stirring with 4.75 g of potassium tert-butylate and the mixture is subsequently heated at 50° for 1 hr. The mixture is left to cool to room temperature, poured into 500 ml of ice-water and stirred for a further 30 min. The suspension is suction filtered, the filter residue is washed three times with 100 ml of water each time and three times with 100 ml of hexane each time and dried. Recrystallization of the crude product from ethyl acetate/hexane yields 14.8 g (90%) of ethyl 1-cyclohexyl-7-iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylate as a colourless solid. M.p. 169°-171° C.

Workup

  1. additionis treated portionwise at room temperature
  2. temperaturethe mixture is subsequently heated at 50° for 1 hr
  3. waitThe mixture is left
  4. filtrationsuction filtered
  5. washthe filter residue is washed three times with 100 ml of water each time and three times with 100 ml of hexane each time
  6. customdried
  7. customRecrystallization of the crude product from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b71eb2ff9d4b469aadec2ccfb87e15e9
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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