Benzyloxyamine hydrochloride → 1-benzyloxy-2-propyl-1H-imidazo[4,5-c]quinoline

HRID 2105460Notes

Reaction equation

HRID 2105460 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[NH:12][C:13](=O)[CH2:14][CH2:15][CH3:16].Cl.[CH2:19]([O:26][NH2:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C>[CH2:19]([O:26][N:27]1[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]=[CH:4][C:3]=2[N:12]=[C:13]1[CH2:14][CH2:15][CH3:16])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 102312Benzyloxyamine hydrochlorideHCID 57447109HCID 57447109, compound

Product 1

HCID 675064061-benzyloxy-2-propyl-1H-imidazo[4,5-c]quinolineYield 29.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(4-chloroquinolin-3-yl)butyramide (3.3 g, 13 mmol, 1.0 eq) and O-benzylhydroxylamine hydrochloride (4.23 g, 26.5 mmol, 2.0 eq) in ethanol (150 mL) was heated at reflux for 3 hours. The reaction mixture was concentrated under reduced pressure. The residue was diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by column chromatography (silica gel eluting with 3% methanol in dichloromethane) to provide 1.20 g of 1-benzyloxy-2-propyl-1H-imidazo[4,5-c]quinoline.

Workup

  1. temperatureat reflux for 3 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was diluted with dichloromethane
  4. washwashed with saturated aqueous sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel eluting with 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-4764ffd81499413cb32566c89cd248a3
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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