Ethyl orthopropionate → HCID 68539371, compound

HRID 1992587Notes

Reaction equation

HRID 1992587 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18])=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl.N1C=C[CH:23]=[CH:22][CH:21]=1.C(OCC)(OCC)(OCC)CC>C1(C)C=CC=CC=1.ClC(Cl)C>[CH2:22]([C:23]1[N:12]([CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[CH3:21]

Participants

6

Reactant 3

HCID 66995Ethyl orthopropionateHCID 10176127Pyridinium chlorideHCID 68536762HCID 68536762, compound

Product 1

HCID 68539371HCID 68539371, compoundYield 904.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 2-{2-[(3-aminoquinolin-4-yl)amino]ethoxy}ethanol (43.0 g, 155 mmol) and pyridine hydrochloride (1.79 g, 15.5 mmol) in toluene (200 mL) and dichloroethane (100 mL) was heated at reflux until a solution formed. The solution was allowed to cool to room temperature, then was cooled to 0° C. Triethyl orthopropionate (30.1 g, 171 mmol) was added and the mixture was heated at reflux for 3 hours. The solution was allowed to cool to room temperature and was concentrated under reduced pressure. The residue was diluted with chloroform, and 4 M NaOH was added to adjust the pH to 9. A solid formed. The mixture was filtered, and the isolated solid dissolved when it was washed with water and chloroform. The filtrate was transferred to a separatory funnel and washed twice with brine. The combined aqueous layers were back-extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated to provide 40.0 g of 2-[2-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]ethanol as a tan solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux until a solution
  3. customformed
  4. temperaturewas cooled to 0° C
  5. temperaturethe mixture was heated
  6. temperatureat reflux for 3 hours
  7. temperatureto cool to room temperature
  8. concentrationwas concentrated under reduced pressure
  9. additionThe residue was diluted with chloroform, and 4 M NaOH
  10. additionwas added
  11. customA solid formed
  12. filtrationThe mixture was filtered
  13. dissolutionthe isolated solid dissolved when it
  14. washwas washed with water and chloroform
  15. customThe filtrate was transferred to a separatory funnel
  16. washwashed twice with brine
  17. extractionThe combined aqueous layers were back-extracted with dichloromethane
  18. dry with materialThe combined organic layers were dried over magnesium sulfate
  19. filtrationfiltered
  20. concentrationconcentrated

Sources & evidence

ORD record
ord-6c6d44d72fa349e5a41170161ad3e0fc
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

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