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

HRID 523131Notes

Reaction equation

HRID 523131 reaction equation
[CH2:1]([O:3][P:4]([C:9]([C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([CH:22]=O)=[N:19]2)=[CH:14][C:13]=1[Br:24])([F:11])[F:10])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].Cl.[NH2:26][OH:27].C([O-])(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)C>[CH2:1]([O:3][P:4]([C:9]([C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18](/[CH:22]=[N:26]/[OH:27])=[N:19]2)=[CH:14][C:13]=1[Br:24])([F:11])[F:10])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

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-90b9bde1f2bd425c8699a4f25c45c6ba
Source dataset
uspto-grants-2016_05
Patent number
US09334295B2

Reaction notes

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