Acetic Acid → N-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylideneamine

HRID 1373960Notes

Reaction equation

HRID 1373960 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([NH2:22])[C:20]([CH2:23][O:24][CH2:25][CH3:26])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:29](OC)([CH3:31])[CH3:30].C(O)(=O)C>C(#N)C.C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([N:22]=[C:29]([CH3:31])[CH3:30])[C:20]([CH2:23][O:24][CH2:25][CH3:26])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 64952,2-DimethoxypropaneHCID 210757477-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-amine

Product 1

HCID 21075798N-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylideneamineYield 100%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-amine (6.91 g, 19.8 mmol) in 55 mL of acetonitrile was treated with 2,2-dimethoxypropane (12.2 mL, 99.2 mmol) and 14 mL of glacial acetic acid. The reaction mixture was heated to 100° C. under an atmosphere of nitrogen. After 22 h, the reaction was cooled to ambient temperature and concentrated under reduced pressure to yield a brown oil. The oil was dissolved in 125 mL of CHCl3 and washed with saturated NaHCO3 solution (2×30 mL) and water (30 mL). The combined aqueous washes were back-extracted with CHCl3 (25 mL). The combined organic extracts were washed with brine (50 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield 7.69 g of N-(7-benzyloxy-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylideneamine as a brown solid.

Workup

  1. temperaturethe reaction was cooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. customto yield a brown oil
  4. washwashed with saturated NaHCO3 solution (2×30 mL) and water (30 mL)
  5. extractionThe combined aqueous washes were back-extracted with CHCl3 (25 mL)
  6. washThe combined organic extracts were washed with brine (50 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-968fbfba256e48c7b570aa1778666d53
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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