Propylene Oxide → HCID 12763958, compound

HRID 1277957Notes

Reaction equation

HRID 1277957 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([Cl:12])=[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>[Cl:12][C:6]1[CH:5]=[C:4]2[C:9]([CH:10]=[CH:11][C:2]3[N:3]2[CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:1]=3)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 66144Ethyl bromopyruvateHCID 127639577-Chloroquinolin-2-amine

Product 1

HCID 12763958HCID 12763958, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

2.0 g of 2-amino-7-chloroquinoline [Chem. Abs., Vol. 79, p. 92024t] were dissolved in 40 ml of dimethoxyethane and then a mixture of 2.5 g of ethyl bromopyruvate and 0.5 g of propylene oxide in 5 ml of dimethoxyethane was added thereto. The mixture obtained was allowed to stand at room temperature for 1 hour and the quaternary salt thus precipitated was filtered off, washed with ether and then was dissolved in 50 ml of ethanol. The solution was refluxed for 1 hour and on subsequent cooling in ice, the solution precipitated ethyl 8-chlorimidazo-[1,2-a]-quinoline-2-carboxylate hydrobromide as pale lemon hygroscopic crystals. This salt was partitioned between 50 ml of dilute sodium carbonate solution and 100 ml of chloroform and the organic solution was separated, washed with 50 ml of water, dried over MgSO4 and was evaporated to dryness under reduced pressure. The residue was crystallized from chloroform/diethyl ether to give colorless crystals of ethyl 8-chloroimidazo-[1,2-a]-quinoline-2-carboxylate melting at 221°-222° C.

Workup

  1. additionwas added
  2. customThe mixture obtained
  3. customthe quaternary salt thus precipitated
  4. filtrationwas filtered off
  5. washwashed with ether
  6. dissolutionwas dissolved in 50 ml of ethanol
  7. temperatureThe solution was refluxed for 1 hour
  8. temperatureon subsequent cooling in ice
  9. customthe solution precipitated ethyl 8-chlorimidazo-[1,2-a]-quinoline-2-carboxylate hydrobromide as pale lemon hygroscopic crystals
  10. customThis salt was partitioned between 50 ml of dilute sodium carbonate solution and 100 ml of chloroform
  11. customthe organic solution was separated
  12. washwashed with 50 ml of water
  13. dry with materialdried over MgSO4
  14. customwas evaporated to dryness under reduced pressure
  15. customThe residue was crystallized from chloroform/diethyl ether

Sources & evidence

ORD record
ord-a09f149239a84e8396d51e46c2226b00
Source dataset
uspto-grants-1981_07
Patent number
US04279912

Reaction notes

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