Ethanol → HCID 67506135, compound

HRID 2105470Notes

Reaction equation

HRID 2105470 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)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.[CH3:22][O:23][NH2:24].C(O)(C)C.C(O)C>C(OCC)(=O)C>[CH3:22][O:23][N:24]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[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 3776Isopropanol2×HCID 521874O-Methylhydroxylamine hydrochlorideHCID 67506372HCID 67506372, compound

Product 1

HCID 67506135HCID 67506135, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-(4-chloroquinolin-3-yl)benzamide (0.020 g, 1 eq), O-methylhydroxylamine hydrochloride (3 eq), and isopropanol was heated at 80° C. for 17 hours. The reaction was also run using ethanol in lieu of isopropanol. The two reaction mixtures were combined, diluted with ethyl acetate, washed sequentially with aqueous potassium carbonate (×2), water, and brine, dried over potassium carbonate, filtered, and then concentrated under reduced pressure. The resulting solid was dried at 80° C. for 3 days to provide 12.1 mg of 1-methoxy-2-phenyl-1H-imidazo[4,5-c]quinoline as a tan powder, mp 194.0-195° C. MS (APCI) m/z 276 (M+H)+; Anal. calcd for C17H13N3O.0.2H2O: C, 73.21; H, 4.84; N, 15.07. Found: C, 73.27; H, 4.61; N, 14.84.

Workup

  1. customThe two reaction mixtures
  2. washwashed sequentially with aqueous potassium carbonate (×2), water, and brine
  3. dry with materialdried over potassium carbonate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting solid was dried at 80° C. for 3 days

Sources & evidence

ORD record
ord-6ece33135f80455e8a6cd59bd83f79f3
Source dataset
uspto-grants-2009_08
Patent number
US07579359B2

Reaction notes

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