Hydroxyamine hydrochloride → Tert-butyl 5-(2-(4-fluorophenyl)-6-((hydroxyimino)methyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate

HRID 927278Notes

Reaction equation

HRID 927278 reaction equation
Cl.[NH2:2][OH:3].[F:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH:32]=O)[CH:17]=3)[C:12]2=[O:34])=[CH:7][CH:6]=1.C([O-])(=O)C.[Na+]>C(O)C.ClCCl>[F:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH:32]=[N:2][OH:3])[CH:17]=3)[C:12]2=[O:34])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 118558140Tert-butyl 5-(2-(4-fluorophenyl)-6-formyl-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate

Product 1

HCID 118558147Tert-butyl 5-(2-(4-fluorophenyl)-6-((hydroxyimino)methyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoateYield 99.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Hydroxylamine hydrochloride (314 mg, 4.52 mmol) was added to a stirred, room temperature mixture of tert-butyl 5-(2-(4-fluorophenyl)-6-formyl-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate (638 mg, 1.507 mmol) and sodium acetate (742 mg, 9.04 mmol) in ethanol (10 mL), and the mixture was stirred at room temperature for 1 h. The mixture was diluted with dichloromethane (60 mL), washed with brine (saturated, 1×30 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure to give tert-butyl 5-(2-(4-fluorophenyl)-6-((hydroxyimino)methyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate (658 mg, 1.501 mmol) as a white solid.

Workup

  1. washwashed with brine (saturated, 1×30 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f87cbf593d344843912fd1fd915b6f88
Source dataset
uspto-grants-2016_03
Patent number
US09290454B2

Reaction notes

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