Water → HCID 136390993, compound

HRID 511833Notes

Reaction equation

HRID 511833 reaction equation
[F:1][C:2]([F:17])([F:16])[CH2:3][O:4][C:5]1[CH:6]=[N:7][C:8]2[C:9](=O)[CH2:10][CH2:11][CH2:12][C:13]=2[CH:14]=1.Cl.[NH2:19][OH:20].C([O-])(=O)C.[Na+].O>C(O)C.O>[F:1][C:2]([F:17])([F:16])[CH2:3][O:4][C:5]1[CH:6]=[N:7][C:8]2[C:9](=[N:19][OH:20])[CH2:10][CH2:11][CH2:12][C:13]=2[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 67291144HCID 67291144, compound

Product 1

HCID 136390993HCID 136390993, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of 3-(2,2,2-trifluoroethoxy)-6,7-dihydroquinolin-8(5H)-one (155 mg, 0.63 mmol), hydroxylamine hydrochloride (88 mg, 1.3 mmol), and sodium acetate (104 mg, 1.3 mmol) in ethanol-water (3:1, 4 mL) was refluxed with stirring for 2 hours. After cooling to room temperature, the mixture was poured into water, and the aqueous layer was extracted with dichloromethane (twice). The combined organic layers were dried over Magnesium sulfate and concentrated in vacuo to give 167 mg of the crude title compound as a brown solid. This was used for the next step without purification:

Workup

  1. temperaturewas refluxed
  2. extractionthe aqueous layer was extracted with dichloromethane (twice)
  3. dry with materialThe combined organic layers were dried over Magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8878481d891447ecbfb5f04899259dc7
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

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