Hydroxyamine hydrochloride → HCID 86759575, compound

HRID 2307439Notes

Reaction equation

HRID 2307439 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18](=O)[CH3:19])[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][CH:14]=[C:15]([C:18](=[N:21][OH:22])[CH3:19])[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 67550478HCID 67550478, compound

Product 1

HCID 86759575HCID 86759575, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 7-acetyl-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester (1.2 g, 4.35 mmol) in EtOH was treated with NH2OH.HCl (0.57 g, 8 mmol). The resulting solution was stirred at 23° C. for 3 h in presence of Amberlist A-21 (2.0 g). The mixture was filtered and the solvent was evaporated. The residue was dissolved in EtOAc, washed with aqueous NaHCO3 and then brine. After drying (MgSO4), the organic layer was evaporated and the crude oxime was purified by chromatography (SiO2, 10-25% EtOAc in hexane) to give 1.08 g (86%) of the title compound as a white solid (m.p: 134-37° C.).

Workup

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

Sources & evidence

ORD record
ord-b3bc9d63ceee4d678c6bc2065f7a455d
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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