Hydroxyamine hydrochloride → HCID 86589153, compound

HRID 2307441Notes

Reaction equation

HRID 2307441 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18](=O)[CH3:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:21][OH:22].Cl>CCO>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18](=[N:21][OH:22])[CH3:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 69845158tert-butyl 6-acetyl-3,4-dihydro-2H-quinoline-1-carboxylate

Product 1

HCID 86589153HCID 86589153, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-acetyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (1.38 g, 5 mmol) in EtOH (20 mL) was treated with NH2OH.HCl (695 mg, 10 mmol). The resulting solution was stirred at 23° C. for 3 hours in the presence of Amberlist A-21 (2.0). Then the mixture was filtered and the solvent evaporated. The residue was dissolved in EtOAc, washed with aqueous NaHCO3 and then brine. After drying (MgSO4), the organic layer was concentrated and the crude oxime purified by chromatography (SiO2, 10-25% EtOAc in hexane) to give 1.4 g (90%) of the title compound as a white solid. m.p: 127-129° C.

Workup

  1. filtrationThen the mixture was filtered
  2. customthe solvent evaporated
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with aqueous NaHCO3
  5. dry with materialAfter drying (MgSO4)
  6. concentrationthe organic layer was concentrated
  7. customthe crude oxime purified by chromatography (SiO2, 10-25% EtOAc in hexane)

Sources & evidence

ORD record
ord-677ad4d5aa874f989daa6140617a5a07
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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