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

HRID 1004172Notes

Reaction equation

HRID 1004172 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 CH2Cl2 (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 CH2Cl2 (30 mL)

Sources & evidence

ORD record
ord-2f0da5f565974d178da147cae590cd61
Source dataset
uspto-grants-2000_04
Patent number
US06048880

Reaction notes

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