2,2-Dimethoxypropane → HCID 21075812, compound

HRID 1373938Notes

Reaction equation

HRID 1373938 reaction equation
[CH2:1]([C:4]1[N:5]([NH2:17])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3].CO[C:20](OC)([CH3:22])[CH3:21]>C(#N)C.C(O)(=O)C.C(Cl)(Cl)Cl>[C:20](=[N:17][N:5]1[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=[C:4]1[CH2:1][CH2:2][CH3:3])([CH3:22])[CH3:21]

Participants

6

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 21075721HCID 21075721, compound

Product 1

HCID 21075812HCID 21075812, compoundYield 78.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-propyl-1H-imidazo[4,5-c]quinolin-1-amine (4.64 g, 20.5 mmol) in 60 mL of acetonitrile and 15 mL of glacial acetic acid was treated with 2,2-dimethoxypropane (12.6 mL, 103 mmol) and heated to 100° C. under an atmosphere of nitrogen. After 6 d, the reaction mixture was concentrated under reduced pressure to yield a brown oil. The oil was dissolved in 100 mL of CHCl3 and washed with 10% Na2CO3 (2×25 mL), water (25 mL), brine (25 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give 4.30 g of N-isopropylidene-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)amine as a brown oil.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customto yield a brown oil
  3. washwashed with 10% Na2CO3 (2×25 mL), water (25 mL), brine (25 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8fa3b2e2c8744a3aa6493bfb9844c082
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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