Pyridine → 4-Bromo-5-nitro-thiophene-2-carbaldehyde oxime

HRID 2216184Notes

Reaction equation

HRID 2216184 reaction equation
Cl.[NH2:2][OH:3].[Br:4][C:5]1[CH:6]=[C:7]([CH:13]=O)[S:8][C:9]=1[N+:10]([O-:12])=[O:11].N1C=CC=CC=1>CCO>[Br:4][C:5]1[CH:6]=[C:7]([CH:13]=[N:2][OH:3])[S:8][C:9]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 218862814-Bromo-5-nitrothiophene-2-carbaldehyde

Product 1

HCID 738521524-Bromo-5-nitro-thiophene-2-carbaldehyde oximeYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (85 g, 1.2 mol) was added to a solution of 4-bromo-5-nitro-thiophene-2-carbaldehyde (234 mg, 0.529 mmol, Example 286: step a) in EtOH (7.5 mL, 200 proof—anhydrous):pyridine (100 mL, anhydrous) at rt over 5 min. The reaction mixture was heated to reflux overnight, then cooled to rt. The solvents were removed in vacuo resulting in a solid residue that was washed with water and filtered. The solid was dried overnight under high vacuum to afford the title compound as a yellow solid (225 g, 88%). The solid was used for the next step without further characterization.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customThe solvents were removed in vacuo
  4. customresulting in a solid residue that
  5. washwas washed with water
  6. filtrationfiltered
  7. customThe solid was dried overnight under high vacuum

Sources & evidence

ORD record
ord-593ab75ba96d4ed096ac1ee64977a991
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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