Hydroxyamine hydrochloride → HCID 74423706, compound

HRID 2244076Notes

Reaction equation

HRID 2244076 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[C:5]([C:13](=O)[CH3:14])=[CH:4][N:3]=1.Cl.[NH2:17][OH:18].CC([O-])=O.[Na+]>CO.O>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[C:5]([C:13](=[N:17][OH:18])[CH3:14])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 25059694HCID 25059694, compound

Product 1

HCID 74423706HCID 74423706, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-(1-amino-6-fluoro-isoquinolin-4-yl)-ethanone (0.8 g, 1 eq), hydroxylamine hydrochloride (1.36 g, 5 eq), and NaOAc (1.6 g. 5 eq) in MeOH (70 mL) and H2O (70 mL) is stirred at RT over 3-day, then concentrated to remove MeOH, poured into Sat'd NaHCO3 aq. (300 mL), extracted by dichloromethane (3×150 mL), dried over Na2SO4, filtered, concentrated to give product 1-(1-amino-6-fluoro-isoquinolin-4-yl)-ethanone oxime (0.75 g, 87%). LC/MS m/z=220 [M+H]+.

Workup

  1. concentrationconcentrated
  2. customto remove MeOH
  3. additionpoured into Sat'd NaHCO3 aq. (300 mL)
  4. extractionextracted by dichloromethane (3×150 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e67de192c1364a5da221923a4bcc0340
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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