Methanol → HCID 57538825, compound

HRID 2105489Notes

Reaction equation

HRID 2105489 reaction equation
ClC(Cl)(Cl)C([N:5]=C=O)=O.[CH:10]([C:13]1[N:14]([O:27][CH3:28])[C:15]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N+:18]([O-])=[CH:17][C:16]=2[N:26]=1)([CH3:12])[CH3:11].CO>ClCCl>[CH:10]([C:13]1[N:14]([O:27][CH3:28])[C:15]2[C:24]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:18]=[C:17]([NH2:5])[C:16]=2[N:26]=1)([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 76400Trichloroacetyl isocyanateHCID 67506960HCID 67506960, compound

Product 1

HCID 57538825HCID 57538825, compoundYield 12.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trichloroacetyl isocyanate (3.3 mL, 28 mmol) was added to a solution of 2-isopropyl-1-methoxy-5-oxido-1H-imidazo[4,5-c]quinoline (4.7 g, 118 mmol) in dichloromethane (100 mL), and the reaction was stirred three hours at room temperature. Methanol (20 mL) was added, and the mixture was stirred for 15 minutes and concentrated under reduced pressure. The residue was dissolved in methanol (25 mL), and sodium methoxide (0.5 mL of a 4.5 N solution in methanol) was added. The mixture was stirred at room temperature for three days and concentrated under reduced pressure. The residue was stirred with dichloromethane (25 mL). A solid was present and was collected by filtration, recrystallized from methanol/water, and dried overnight in a vacuum oven at 70° C. to provide 0.878 g of 2-isopropyl-1-methoxy-1H-imidazo[4,5-c]quinolin-4-amine as tan needles, mp 217-219° C.

Workup

  1. stirringthe mixture was stirred for 15 minutes
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in methanol (25 mL)
  4. additionsodium methoxide (0.5 mL of a 4.5 N solution in methanol) was added
  5. stirringThe mixture was stirred at room temperature for three days
  6. concentrationconcentrated under reduced pressure
  7. stirringThe residue was stirred with dichloromethane (25 mL)
  8. filtrationwas collected by filtration
  9. customrecrystallized from methanol/water
  10. customdried overnight in a vacuum oven at 70° C.

Sources & evidence

ORD record
ord-ac99eb913f5c49288c4e1ee5af9edd49
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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