Hydroxylamine → HCID 135436619, compound

HRID 2053419Notes

Reaction equation

HRID 2053419 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]1[O:17][N:16]=[C:15]([CH:18]=O)[CH:14]=1)=[C:5]2[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[NH2:26]O.C(OC(=O)C)(=O)C>CO.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]1[O:17][N:16]=[C:15]([C:18]#[N:26])[CH:14]=1)=[C:5]2[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 7918Acetic AnhydrideHCID 136338674HCID 136338674, compound

Product 1

HCID 135436619HCID 135436619, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

To a solution of 5-(6-chloro-2-oxo-4-phenyl-1,2-dihydro-quinolin-3-yl)-isoxazole-3-carboxaldehyde in MeOH (20 mL), aq. NH2OH (1 mmol) was added. The resulting mixture was stirred at RT for 2 hr. The reaction mixture was concentrated and water (20 mL) was added. The precipitate formed was then collected by suction filtration and dried in vacuo. Above oxime (365 mg, 1 mmol) was dissolved in pyridine (10 mL) and acetic anhydride (0.3 mL, 2 mmol) was added. The resulting mixture was stirred overnight and concentrated. The residue obtained was purified with (30% EtOAc:Hexane) to obtain the title compound. Yield 67%.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater (20 mL) was added
  3. customThe precipitate formed
  4. filtrationwas then collected by suction filtration
  5. customdried in vacuo
  6. stirringThe resulting mixture was stirred overnight
  7. concentrationconcentrated
  8. customThe residue obtained
  9. customwas purified with (30% EtOAc:Hexane)

Sources & evidence

ORD record
ord-d1828cf29a9c40c7bb6801239d91338e
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

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