2,2-Dimethoxypropane → HCID 21075782, compound

HRID 1373944Notes

Reaction equation

HRID 1373944 reaction equation
[N:1]1([NH2:14])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.CO[C:17](OC)([CH3:19])[CH3:18]>C(#N)C.C(O)(=O)C.C(Cl)(Cl)Cl>[N:1]1([N:14]=[C:17]([CH3:19])[CH3:18])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 21075713HCID 21075713, compound

Product 1

HCID 21075782HCID 21075782, compoundYield 100.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 1H-imidazo[4,5-c]quinolin-1-amine (2.86 g, 15.5 mmol) in 60 mL of acetonitrile and 15 mL of glacial acetic acid was treated with 2,2-dimethoxypropane (9.53 mL, 77.5 mmol) and heated to 100° C. under an atmosphere of nitrogen. After 18 h, the reaction mixture was concentrated under reduced pressure to give a brown oil. The oil was dissolved in 100 mL of CHCl3 and washed with 5% Na2CO3 solution (2×30 mL), water (30 mL) and brine (30 mL). The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure to yield 3.48 g of N-(1H-imidazo[4,5-c]quinolin-1-yl)isopropylideneamine as a brown oil.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customto give a brown oil
  3. washwashed with 5% Na2CO3 solution (2×30 mL), water (30 mL) and brine (30 mL)
  4. dry with materialThe organic portion was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e559613019ad4aeba8ff7dcf318d1763
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

Loading…