Hydrochloric Acid → HCID 58837346, compound

HRID 521280Notes

Reaction equation

HRID 521280 reaction equation
Cl.[CH3:2][C:3]1[N:4]([CH2:17][CH2:18][CH2:19][C:20]2([CH3:25])OCC[O:21]2)[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[C:7]([NH2:15])[C:6]=2[N:16]=1.C(=O)([O-])[O-].[K+].[K+]>O.ClCCl>[NH2:15][C:7]1[C:6]2[N:16]=[C:3]([CH3:2])[N:4]([CH2:17][CH2:18][CH2:19][C:20](=[O:21])[CH3:25])[C:5]=2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 58837334HCID 58837334, compound

Product 1

HCID 58837346HCID 58837346, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Concentrated hydrochloric acid (3 mL) was added to 2-methyl-1-[3-(2-methyl-[1,3]dioxolan-2-yl)propyl]-1H-imidazo[4,5-c]quinolin-4-amine (1.0 g, 2.7 mmol), and the mixture stirred for a few minutes until everything was in solution. Water (5 mL) was then added and the solution stirred for one hour at room temperature. After the addition of dichloromethane (75 mL) and water (25 mL), the solution was made basic by the slow addition of potassium carbonate (10.0 g). The layers were separated, and the organic layer was washed with a saturated aqueous sodium bicarbonate solution (25 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 5-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one, mp 194-196° C.

Workup

  1. stirringthe solution stirred for one hour at room temperature
  2. customThe layers were separated
  3. washthe organic layer was washed with a saturated aqueous sodium bicarbonate solution (25 mL)
  4. dry with materialdried over potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f0b55a854b34a8aa4cf2ccd58e350b4
Source dataset
uspto-grants-2016_05
Patent number
US09328110B2

Reaction notes

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