Pyridine → 2,5-Di(4-pyridyl)-4-methylthiophene-3-carbaldehyde oxime dihydrochloride

HRID 2121721Notes

Reaction equation

HRID 2121721 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[S:8][C:9]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[C:10]([CH3:14])[C:11]=2[CH:12]=O)=[CH:3][CH:2]=1.[ClH:21].[NH2:22][OH:23].N1C=CC=CC=1>CO>[ClH:21].[ClH:21].[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[S:8][C:9]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[C:10]([CH3:14])[C:11]=2[CH:12]=[N:22][OH:23])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 121127812,5-Di(4-pyridyl)-4-methylthiophene-3-carbaldehyde

Product 1

HCID 1363810572,5-Di(4-pyridyl)-4-methylthiophene-3-carbaldehyde oxime dihydrochlorideYield 42.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2,5-di(4-pyridyl)-4-methylthiophene-3-carbaldehyde (0.14 g), hydroxylamine hydrochloride (0.04 g), and pyridine (0.04 mL) in MeOH (3 mL) was heated at reflux temperature for 16 hours. After cooling, the volatiles were removed by evaporation. The resulting residue was dissolved in 10% methanolic HCl (5 mL) and the solution was concentrated in vacuo again. The resulting solid was washed with water (50 mL) and CH2CI2 (30 mL) to provide the title compound (0.045 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 16 hours
  3. temperatureAfter cooling
  4. customthe volatiles were removed by evaporation
  5. dissolutionThe resulting residue was dissolved in 10% methanolic HCl (5 mL)
  6. concentrationthe solution was concentrated in vacuo again
  7. washThe resulting solid was washed with water (50 mL) and CH2CI2 (30 mL)

Sources & evidence

ORD record
ord-c629766415a54bbc802668f06efa987d
Source dataset
uspto-grants-2004_02
Patent number
US06696470B2

Reaction notes

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