Hydroxyamine hydrochloride → N-{[5-(3,4-Dimethoxyphenyl)furan-2-yl]methylidene}hydroxylamine

HRID 1759147Notes

Reaction equation

HRID 1759147 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[O:15][C:14]([CH:16]=O)=[CH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl.[NH2:19][OH:20].C([O-])(=O)C.[Na+]>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[O:15][C:14]([CH:16]=[N:19][OH:20])=[CH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 123749575-(3,4-Dimethoxyphenyl)furan-2-carbaldehyde

Product 1

HCID 71382179N-{[5-(3,4-Dimethoxyphenyl)furan-2-yl]methylidene}hydroxylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-(3,4-Dimethoxyphenyl)furaldehyde (100 g, 0.43 mole), hydroxylamine hydrochloride (59.9 g, 0.86 mole) and anhydrous sodium acetate (70.69 g) was treated with solution of water (150 ml) in SDA #32 (2200 ml). The reaction mixture was heated at reflux for 6 hours. The mixture was filtered hot and the filtrate chilled. The intermediate was collected and used without further purification in Part B; 38 g (36%), m.p. 148°.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 6 hours
  3. filtrationThe mixture was filtered hot
  4. temperaturethe filtrate chilled
  5. customThe intermediate was collected
  6. customused without further purification in Part B

Sources & evidence

ORD record
ord-9018013a114e49e08602f79164eccfdd
Source dataset
uspto-grants-1982_07
Patent number
US04339386

Reaction notes

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