Hydroxyamine hydrochloride → (NE)-N-[[6-bromo-7-[diethoxyphosphoryl(difluoro)methyl]quinolin-2-yl]methylidene]hydroxylamine

HRID 448806Notes

Reaction equation

HRID 448806 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([P:15](=[O:22])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])([F:14])[F:13])[N:8]=[C:7]([CH:23]=O)[CH:6]=[CH:5]2.Cl.[NH2:26][OH:27].C([O-])(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([P:15](=[O:22])([O:16][CH2:17][CH3:18])[O:19][CH2:20][CH3:21])([F:13])[F:14])[N:8]=[C:7](/[CH:23]=[N:26]/[OH:27])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 86638323HCID 86638323, compound

Product 1

HCID 136390154(NE)-N-[[6-bromo-7-[diethoxyphosphoryl(difluoro)methyl]quinolin-2-yl]methylidene]hydroxylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of diethyl [(6-bromo-2-formylquinolin-7-yl)(difluoro)methyl]phosphonate (525 mg, 1.244 mmol) [Example 8, Step 4] in ethanol (12 mL) at room temperature were added hydroxylamine hydrochloride (130 mg, 1.865 mmol) and sodium acetate (508 mg. 3.73 mmol). The reaction mixture was stirred at 70° C. for 1 hour. It was then poured into aqueous sodium hydrogen carbonate and extracted with ethyl acetate (100 mL), washed with aqueous sodium hydrogen carbonate (2×), brine, dried with MgSO4, and concentrated in vacuo to give crude diethyl [(6-bromo-2-[(E)-(hydroxyimino)methyl]quinolin-7-yl)(difluoro)methyl]phosphonate.

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. washwashed with aqueous sodium hydrogen carbonate (2×), brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2763090109634b018c36302ba5638d8c
Source dataset
uspto-grants-2013_07
Patent number
US08481742B2

Reaction notes

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