Hydroxyamine hydrochloride → 5-Bromo-2-nitrothiophene-3-carbaldehyde oxime

HRID 385712Notes

Reaction equation

HRID 385712 reaction equation
[Br:1][C:2]1[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([CH:10]=O)[CH:3]=1.Cl.[NH2:13][OH:14].C([O-])(=O)C.[Na+]>C(O)C>[Br:1][C:2]1[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([CH:10]=[N:13][OH:14])[CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 534029475-Bromo-2-nitrothiophene-3-carbaldehyde

Product 1

HCID 723159975-Bromo-2-nitrothiophene-3-carbaldehyde oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Bromo-2-nitrothiophene-3-carbaldehyde (22.5 g, 95 mmol), hydroxylamine hydrochloride (6.96 g, 100 mmol) and sodium acetate (8.21 g, 100 mmol) were stirred in ethanol (225 mL) at room temperature overnight. The solvent was removed in vacuo, saturated NaHCO3 was added and the products extracted into EtOAc (3×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give the title compound as an orange solid.

Workup

  1. customThe solvent was removed in vacuo, saturated NaHCO3
  2. additionwas added
  3. extractionthe products extracted into EtOAc (3×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4691dfd4a98b4a58809149e9cf146357
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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