Methanol → HCID 21075811, compound

HRID 1373894Notes

Reaction equation

HRID 1373894 reaction equation
Cl.[CH3:2][C:3]1[N:4]([NH2:16])[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=1.[C:17]1(C)[CH:22]=CC(S(O)(=O)=O)=C[CH:18]=1.O.CO>COC(OC)(C)C>[C:17](=[N:16][N:4]1[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=[C:3]1[CH3:2])([CH3:22])[CH3:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 21075719HCID 21075719, compound

Product 1

HCID 21075811HCID 21075811, compoundYield 1,461.4%

Reagents, catalysts & solvents 1

HCID 64952,2-DimethoxypropaneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 2-methyl-1H-imidazo[4,5-c]quinolin-1-amine hydrochloride (1.79 g, 7.62 mmol) in 30 mL of 2,2-dimethoxypropane was treated with 90 mg of p-toluenesulfonic acid. The reaction mixture was heated to 100° C. overnight. The reaction mixture was then treated with 10 mL of H2O and 10 mL of MeOH, and heating was continued for 24 h. The reaction mixture was cooled and concentrated under reduced pressure. The resulting oil was dissolved in 50 mL of CHCl3 and washed with 2% Na2CO3 solution, H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated to give N-isopropylidene(2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)amine (1.82 g) as a yellow solid.

Workup

  1. temperatureheating
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting oil was dissolved in 50 mL of CHCl3
  5. washwashed with 2% Na2CO3 solution, H2O and brine
  6. dry with materialThe organic portion was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e892a1ab1e3f43b686f3ec48debc33f9
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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