2,2-Dimethoxypropane → HCID 21075800, compound

HRID 1373950Notes

Reaction equation

HRID 1373950 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([NH2:15])[C:13]([CH2:16][CH2:17][CH3:18])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1.CO[C:21](OC)([CH3:23])[CH3:22]>C(#N)C.C(O)(=O)C.C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([N:15]=[C:21]([CH3:23])[CH3:22])[C:13]([CH2:16][CH2:17][CH3:18])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1

Participants

6

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 21075753HCID 21075753, compound

Product 1

HCID 21075800HCID 21075800, compoundYield 92.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-amine (17.6 g, 57.7 mmol) in 160 mL of acetonitrile and 40 mL of glacial acetic acid was treated with 2,2-dimethoxypropane (35.5 mL, 288 mmol). The reaction mixture was heated to 100° C. under an atmosphere of nitrogen. After 16 h, the reaction was cooled to ambient temperature and concentrated under reduced pressure to yield a brown oil. The oil was dissolved in CHCl3 (200 mL). The CHCl3 solution was washed with saturated NaHCO3 solution (2×50 mL), water (50 mL) and brine (50 mL). The organic portion was then dried over Na2SO4, filtered and concentrated under reduced pressure to yield 18.4 g of N-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)isopropylideneamine as a red/brown foam.

Workup

  1. temperaturethe reaction was cooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. customto yield a brown oil
  4. washThe CHCl3 solution was washed with saturated NaHCO3 solution (2×50 mL), water (50 mL) and brine (50 mL)
  5. dry with materialThe organic portion was then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ad290944f9b942bfb9739bc3c955a04c
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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