Water → HCID 58909378, compound

HRID 1991545Notes

Reaction equation

HRID 1991545 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[CH2:8][CH2:7][C:6]2=O)[CH3:2].N1C=CC=CC=1.Cl.[NH2:22][OH:23].O>C(O)C.ClCCl>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[CH2:8][CH2:7]/[C:6]/2=[N:22]\[OH:23])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 58909275HCID 58909275, compound

Product 1

HCID 58909378HCID 58909378, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 6-ethyl-1-methyl-2,3-dihydroquinolin-4(1H)-one (0.32 g) in ethanol (25 mL) were added pyridine (0.53 g) and hydroxylamine hydrochloride (0.59 g). The mixture was heated to 90° C. for two hours with a reflux condenser attached. The mixture was cooled to room temperature, and the solvent was stripped under reduced pressure. The residue was portioned between water and dichloromethane and the organics were extracted three times. The combined organics were washed once with brine, dried with sodium sulfate, filtered, and concentrated. 0.34 g of the title product were recovered. (98% yield). MS (ESI+) for C12H16N2O m/z 205.02 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionthe organics were extracted three times
  3. washThe combined organics were washed once with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custom0.34 g of the title product were recovered

Sources & evidence

ORD record
ord-20037fe897d748a19cd8237d81f87e38
Source dataset
uspto-grants-2010_01
Patent number
US07645780B2

Reaction notes

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