Hydrochloric Acid → HCID 58837346, compound

HRID 2362521Notes

Reaction equation

HRID 2362521 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-d66027558ec84264a9fec26cfc13e214
Source dataset
uspto-grants-2014_04
Patent number
US08691837B2

Reaction notes

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