Hydrochloric Acid → HCID 86052969, compound

HRID 1623132Notes

Reaction equation

HRID 1623132 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[N:15]([CH2:16][CH2:17][CH2:18][CH:19](OC)[O:20]C)[C:14]([CH2:24][CH2:25][CH3:26])=[N:13][C:8]=3[CH:9]=[N:10][C:11]=2[CH:12]=1>C1COCC1.O>[Br:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]3[N:15]([CH2:16][CH2:17][CH2:18][CH:19]=[O:20])[C:14]([CH2:24][CH2:25][CH3:26])=[N:13][C:8]=3[CH:9]=[N:10][C:11]=2[CH:12]=1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 69507145HCID 69507145, compound

Product 1

HCID 86052969HCID 86052969, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Concentrated hydrochloric acid (8 mL) was added to a mixture of 7-bromo-1-(4,4-dimethoxybutyl)-2-propyl-1H-imidazo[4,5-c]quinoline (57.0 g, 140.3 mmol) in THF (250 mL) and water (70 mL) and stirred overnight at ambient temperature. Additional concentrated hydrochloric acid (10 mL) was added and the reaction mixture was stirred for 4 hours. The reaction mixture was concentrated under reduced pressure and the residue was diluted with water and neutralized with saturated aqueous sodium bicarbonate solution. The mixture was diluted with 10% methanol in dichloromethane, the phases were separated, and the combined organics were dried over magnesium sulfate and concentrated under reduced pressure to afford 50.3 g of 4-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyraldehyde.

Workup

  1. stirringthe reaction mixture was stirred for 4 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with water and neutralized with saturated aqueous sodium bicarbonate solution
  4. additionThe mixture was diluted with 10% methanol in dichloromethane
  5. customthe phases were separated
  6. dry with materialthe combined organics were dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ec70d611575d4a04a3d98282b62e9b7f
Source dataset
uspto-grants-2014_07
Patent number
US08778963B2

Reaction notes

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