Ethanol → HCID 12763964, compound

HRID 1277956Notes

Reaction equation

HRID 1277956 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][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Br[CH2:17][C:18](=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(O)C>C(COC)OC>[CH:13]([O:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]2[CH:17]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:1]=[C:2]2[CH:11]=1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 66144Ethyl bromopyruvateHCID 14067418HCID 14067418, compound

Product 1

HCID 12763964HCID 12763964, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

2.8 g of 2-amino-4-isopropoxyquinoline were dissolved in 50 ml of dimethoxyethane and 4 g of ethyl bromopyruvate were added thereto. The mixture obtained was allowed to stand at room temperature for 1 hour and then was reduced in volume under vacuum. 50 ml of ethanol were added thereto and the resultant mixture was refluxed for 90 minutes. The ethanol was evaporated off under vacuum and the residue was dissolved in 100 ml of 2 N HCl. The acid solution thus obtained was washed with 50 ml of ethyl acetate and then was made alkaline with sodium carbonate. The mixture was extracted three times with 50 ml of chloroform and the combined chloroform extracts were washed with 100 ml of water, dried over MgSO4 and then was evaporated to dryness under reduced pressure to obtain an orange oil. The oil was purified by column chromatography (silica gel-chloroform as eluant) and then was crystallized from diethyl ether to obtain colorless needles of ethyl 5-isopropoxyimidazo-[1,2-a]-quinoline-2-carboxylate melting at 127°-129° C.

Workup

  1. customThe mixture obtained
  2. customThe ethanol was evaporated off under vacuum
  3. dissolutionthe residue was dissolved in 100 ml of 2 N HCl
  4. customThe acid solution thus obtained
  5. washwas washed with 50 ml of ethyl acetate
  6. extractionThe mixture was extracted three times with 50 ml of chloroform
  7. washthe combined chloroform extracts were washed with 100 ml of water
  8. dry with materialdried over MgSO4
  9. customwas evaporated to dryness under reduced pressure
  10. customto obtain an orange oil
  11. customThe oil was purified by column chromatography (silica gel-chloroform as eluant)
  12. customwas crystallized from diethyl ether

Sources & evidence

ORD record
ord-65caa8a9fbd941f283494070c5493754
Source dataset
uspto-grants-1981_07
Patent number
US04279912

Reaction notes

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