Diethyl Ether → HCID 12763984, compound

HRID 1277972Notes

Reaction equation

HRID 1277972 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[Cl:12])[N:3]=1.Br[CH2:14][C:15](=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17].C1OC1C.CCOCC>C(COC)OC>[Cl:12][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]1[N:3]2[CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:1]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6378Propylene OxideHCID 66144Ethyl bromopyruvateHCID 140674265-Chloroquinolin-2-amine

Product 1

HCID 12763984HCID 12763984, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

140 mg of 2-amino-5-chloroquinoline were dissolved in 2.5 ml of dimethoxyethane and then a mixture of 170 mg of ethyl bromopyruvate and 30 mg of propylene oxide was added. The mixture was stirred at room temperature for 2 hours and 2 ml of ether were added. Then, the mixture was cooled in ice and the precipitated quaternary salt was filtered off, was dissolved in 5 ml of ethanol and the solution was heated at reflux for 2 hours. Then, the solvent was removed under vacuum and the residue was partitioned between sodium bicarbonate solution and chloroform. The chloroform solution was dried over magnesium sulfate and was evaporated to dryness. The residue was chromatographed over silica with chloroform as eluent and the purified product was recrystallized from ethyl acetate/petroleum ether to obtain colorless needles of ethyl 6-chloroimidazo-[1,2-a]-quinoline-2-carboxylate melting at 193°-194° C.

Workup

  1. additionwas added
  2. temperatureThen, the mixture was cooled in ice
  3. filtrationthe precipitated quaternary salt was filtered off
  4. dissolutionwas dissolved in 5 ml of ethanol
  5. temperaturethe solution was heated
  6. temperatureat reflux for 2 hours
  7. customThen, the solvent was removed under vacuum
  8. customthe residue was partitioned between sodium bicarbonate solution and chloroform
  9. dry with materialThe chloroform solution was dried over magnesium sulfate
  10. customwas evaporated to dryness
  11. customThe residue was chromatographed over silica with chloroform as eluent
  12. customthe purified product was recrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-3e35b2e4683447e7b6fdd667d5564f13
Source dataset
uspto-grants-1981_07
Patent number
US04279912

Reaction notes

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