Propylene Oxide → Ethyl 5-bromoimidazo-[1,2-a]-quinoline-2-carboxylate

HRID 1277969Notes

Reaction equation

HRID 1277969 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Br:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Br[CH2:14][C:15](=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17].C1OC1C>C(COC)OC>[Br:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]2[CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:1]=[C:2]2[CH:11]=1

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 66144Ethyl bromopyruvateHCID 140674194-Bromoquinolin-2-amine

Product 1

HCID 12763980Ethyl 5-bromoimidazo-[1,2-a]-quinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1 g of 2-amino-4-bromoquinoline was dissolved in 20 ml of dimethoxyethane and a mixture of 1.5 g of ethyl bromopyruvate and 0.5 g of propylene oxide was added thereto. The solution was allowed to stand at room temperature for 1 hour and the quaternary salt thus precipitated was filtered off, was washed with ether and then was dissolved in 20 ml of ethanol. The solution was refluxed for 1 hour, cooled and then was evaporated to dryness under vacuum. The residue was partitioned between 50 ml of chloroform and 50 ml of 2 N sodium carbonate and the organic extract was washed with 50 ml of water, was dried over MgSO4, and was reduced in volume under vacuum. Then, ether was added thereto to give cream needles of ethyl 5-bromoimidazo-[1,2-a]-quinoline-2-carboxylate melting at 205°-207° C.

Workup

  1. additionwas added
  2. customthe quaternary salt thus precipitated
  3. filtrationwas filtered off
  4. washwas washed with ether
  5. dissolutionwas dissolved in 20 ml of ethanol
  6. temperatureThe solution was refluxed for 1 hour
  7. temperaturecooled
  8. customwas evaporated to dryness under vacuum
  9. customThe residue was partitioned between 50 ml of chloroform and 50 ml of 2 N sodium carbonate
  10. extractionthe organic extract
  11. washwas washed with 50 ml of water
  12. dry with materialwas dried over MgSO4
  13. additionThen, ether was added

Sources & evidence

ORD record
ord-d5aba955bfc34ba0b11ccd5bb94f10c6
Source dataset
uspto-grants-1981_07
Patent number
US04279912

Reaction notes

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