Ethanol → 7-Bromo-2-ethoxymethyl-1-(isopropoxypropyl)-1H-imidazo[4,5-c]quinoline

HRID 909337

Reaction equation

HRID 909337 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:13][CH2:14][CH2:15][CH2:16][O:17][CH:18]([CH3:20])[CH3:19])=[C:7]([NH2:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH2:21]([O:23][CH2:24][C:25](Cl)=O)[CH3:22].C(O)C>C(#N)C.C(N(CC)CC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:13]([CH2:14][CH2:15][CH2:16][O:17][CH:18]([CH3:20])[CH3:19])[C:22]([CH2:21][O:23][CH2:24][CH3:25])=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 84189Ethoxyacetyl chlorideHCID 690787337-bromo-N4-(3-isopropoxypropyl)quinoline-3,4-diamine

Product 1

HCID 673819647-Bromo-2-ethoxymethyl-1-(isopropoxypropyl)-1H-imidazo[4,5-c]quinolineYield 67.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent2×

Procedure

7-Bromo-N4-(3-isopropoxypropyl)quinoline-3,4-diamine (45 g) was dissolved in acetonitrile (1.3 L) and triethylamine (19.4 mL). Ethoxyacetyl chloride (18.0 g) was added dropwise to the solution and the reaction was stirred for 16 hours. The solvent was removed under reduced pressure to afford a tan solid. The solid was added to a solution of ethanol (1 L) and triethylamine (77.5 mL) and heated at reflux for 4 hours. The solvent was removed under reduced pressure. Water was added to the solid residue and the crude product was recovered by filtration. Recrystallization from acetonitrile yielded 36.25 g of 7-bromo-2-ethoxymethyl-1-(3-isopropoxypropyl)-1H-imidazo[4,5-c]quinoline as a tan crystalline solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto afford a tan solid
  3. temperatureheated
  4. temperatureat reflux for 4 hours
  5. customThe solvent was removed under reduced pressure
  6. additionWater was added to the solid residue
  7. filtrationthe crude product was recovered by filtration
  8. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-134fed903e6046ffa77168d789ca7fdf
Source dataset
uspto-grants-2011_09
Patent number
US08017779B2

Linked notes

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