Hydroxyamine hydrochloride → HCID 87202177, compound

HRID 2104495Notes

Reaction equation

HRID 2104495 reaction equation
[C:1]1([C:7]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[C:25]([F:28])([F:27])[F:26])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:30][OH:31].O.O.O.C([O-])(=O)C.[Na+]>CCO.O>[C:1]1(/[C:7](/[C:9]2[CH:10]=[N:11][C:12]3[C:17]([C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[C:25]([F:28])([F:27])[F:26])=[N:30]\[OH:31])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochloride2×HCID 11360909Phenyl[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanoneHCID 23665404Sodium Acetate Trihydrate2×

Product 1

HCID 87202177HCID 87202177, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Phenyl[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone (Example 1, 0.128 g, 0.339 mmol) was taken into EtOH/H2O (7 mL, 7:3 mixture) along with hydroxylamine hydrochloride (0.028 g, 0.407 mmol) and sodium acetate trihydrate (0.061 g, 0.447 mmol) and this mixture was refluxed for 1.5 hours. TLC and LC-MS showed no reaction. Therefore, excess quantities of hydroxylamine hydrochloride and sodium acetate trihydrate were added and refluxing was continued overnight. The reaction was concentrated and the resulting material was taken up into CH2Cl2/H2O. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organics were dried over sodium sulfate and concentrated. The product was purified via column chromatography using 15% ethyl acetate in hexane as the eluent to afford 0.100 g of desired product as a white solid. MS (ESI) m/z 393 ([M+H]+);

Workup

  1. temperaturethis mixture was refluxed for 1.5 hours
  2. customno reaction
  3. temperaturerefluxing
  4. concentrationThe reaction was concentrated
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with CH2Cl2
  7. dry with materialThe combined organics were dried over sodium sulfate
  8. concentrationconcentrated
  9. customThe product was purified via column chromatography

Sources & evidence

ORD record
ord-37664e904dad41e9aecd67c15757dd40
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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