Triethylamine → HCID 12763972, compound

HRID 1277963Notes

Reaction equation

HRID 1277963 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]([CH3:15])[CH3:14])[C:9]2[C:4](=[CH:5][C:6]([Cl:16])=[CH:7][CH:8]=2)[N:3]=1.Br[CH2:18][C:19](=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21].C(N(CC)CC)C>C(COC)OC>[Cl:16][C:6]1[CH:5]=[C:4]2[C:9]([C:10]([O:12][CH:13]([CH3:14])[CH3:15])=[CH:11][C:2]3[N:3]2[CH:18]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:1]=3)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66144Ethyl bromopyruvateHCID 14067427HCID 14067427, compound

Product 1

HCID 12763972HCID 12763972, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1.9 g of 2-amino-7-chloro-4-isopropoxyquinoline were dissolved in 20 ml of dimethoxyethane and 1.9 g of ethyl bromopyruvate were added thereto followed by 800 mg of triethylamine. The mixture obtained was stirred at room temperature for 4 hours and then the solvent was evaporated under vacuum. The residue was dissolved in 100 ml of chloroform and the solution was dried over MgSO4 and was evaporated to dryness under vacuum. The residue was dissolved in 25 ml of ethanol and the solution was refluxed for 3 hours and then the solvent was removed under vacuum. The residue was purified by column chromatography (silica gel-chloroform/methanol eluant) and then was crystallized from diethyl ether to obtain pale cream needles of ethyl 8-chloro-5-isopropoxyimidazo-[1,2-a]-quinoline-2-carboxylate melting at 187°-189° C.

Workup

  1. customThe mixture obtained
  2. customthe solvent was evaporated under vacuum
  3. dissolutionThe residue was dissolved in 100 ml of chloroform
  4. dry with materialthe solution was dried over MgSO4
  5. customwas evaporated to dryness under vacuum
  6. dissolutionThe residue was dissolved in 25 ml of ethanol
  7. temperaturethe solution was refluxed for 3 hours
  8. customthe solvent was removed under vacuum
  9. customThe residue was purified by column chromatography (silica gel-chloroform/methanol eluant)
  10. customwas crystallized from diethyl ether

Sources & evidence

ORD record
ord-f772cae51ccb4094adb4d80130bad626
Source dataset
uspto-grants-1981_07
Patent number
US04279912

Reaction notes

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