Hydrochloric Acid → HCID 57464096, compound

HRID 1623110Notes

Reaction equation

HRID 1623110 reaction equation
C([O:3][CH:4](OCC)[CH2:5][CH2:6][CH2:7][N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:10]=[C:9]1[CH2:21][CH2:22][CH3:23])C.Cl.C(=O)([O-])[O-].[K+].[K+]>O.ClCCl>[CH2:21]([C:9]1[N:8]([CH2:7][CH2:6][CH2:5][CH:4]=[O:3])[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:10]=1)[CH2:22][CH3:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 57455393HCID 57455393, compound

Product 1

HCID 57464096HCID 57464096, compoundYield 113.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-(4,4-diethoxybutyl)-2-propyl-1H-imidazo[4,5-c]quinoline (25.3 g, 71.2 mmol) was added to a solution of concentrated hydrochloric acid (35 mL) and water (35 mL) cooled to 0° C. and the reaction mixture was allowed to warm to ambient temperature and was stirred for 30 minutes. The reaction mixture was diluted with water (100 mL) and dichloromethane (200 mL) and the pH of the reaction mixture was slowly made basic with addition of potassium carbonate. The aqueous and organic layers were separated and the organic layer was dried over potassium carbonate, filtered, and concentrated to afford 22.7 g of 4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyraldehyde.

Workup

  1. temperatureto warm to ambient temperature
  2. customThe aqueous and organic layers were separated
  3. dry with materialthe organic layer was dried over potassium carbonate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0b3f2caad9ae49bba5f89e79ad884fd1
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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