Isopropanol → HCID 67506393, compound

HRID 2105474Notes

Reaction equation

HRID 2105474 reaction equation
Cl.[CH2:2]([O:9][NH2:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[CH:14][C:13]=1[NH:22][C:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(O)(C)C>C(Cl)(Cl)Cl>[CH2:2]([O:9][N:10]1[C:12]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:22]=[C:23]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 102312Benzyloxyamine hydrochlorideHCID 67506372HCID 67506372, compound

Product 1

HCID 67506393HCID 67506393, compoundYield 12.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

O-Benzylhydroxylamine hydrochloride (10.2 g, 63.7 mmol), N-(4-chloroquinolin-3-yl)benzamide (6.00 g, 21.2 mmol), and isopropanol (200 mL) were combined and heated at 80° C. After 18 hours the reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane, and the solution was washed sequentially with saturated aqueous potassium carbonate and water and then concentrated under reduced pressure. This material was purified by column chromatography (320 g of silica gel, eluting with a gradient of 1-2% methanol in dichloromethane). The resulting solid was triturated with hexanes to provide a tan solid that was isolated by filtration. The solid was mixed with chloroform and isolated by filtration to provide 0.951 g of 1-(benzyloxy)-2-phenyl-1H-imidazo[4,5-c]quinoline as a reddish-brown solid. 2-Phenyl-1H-imidazo[4,5-c]quinolin-1-ol (2.39 g) was recovered from the aqueous washings.

Workup

  1. concentrationAfter 18 hours the reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washthe solution was washed sequentially with saturated aqueous potassium carbonate and water
  4. concentrationconcentrated under reduced pressure
  5. customThis material was purified by column chromatography (320 g of silica gel
  6. washeluting with a gradient of 1-2% methanol in dichloromethane)
  7. customThe resulting solid was triturated with hexanes
  8. customto provide a tan solid
  9. customthat was isolated by filtration
  10. customisolated by filtration

Sources & evidence

ORD record
ord-d21530468a224f2d990efdd529ef048b
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

Loading…