1,1-Dimethylhydrazine → 5-methoxy-1-tetralone N,N-dimethylhydrazone

HRID 264539

Reaction equation

HRID 264539 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=O.[CH3:14][N:15]([CH3:17])[NH2:16]>[Cl-].[Na+]>[CH3:14][N:15]([CH3:17])[N:16]=[C:8]1[C:9]2[C:4](=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 59761,1-DimethylhydrazineHCID 366205-Methoxytetralone

Product 1

HCID 2909415-methoxy-1-tetralone N,N-dimethylhydrazoneYield 83%

Reagents, catalysts & solvents 1

HCID 5234Sodium ChlorideSolvent

Procedure

35.25 g of 5-methoxy-1-tetralone and 61 ml of N,N-dimethylhydrazine were heated to about 80° under argon for 5 hours. The mixture was left to cool, 200 ml of 10% sodium chloride solution were added and the mixture was extracted several times with diethyl ether. The mixture was dried over sodium sulfate, filtered and evaporated. The oily residue was distilled over a 10 cm Vigreux column. At 85°-95°/0.1 mbar there were obtained 36.4 g (83%) of 5-methoxy-1-tetralone N,N-dimethylhydrazone as a yellow oil.

Workup

  1. waitThe mixture was left
  2. temperatureto cool
  3. extractionthe mixture was extracted several times with diethyl ether
  4. dry with materialThe mixture was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. distillationThe oily residue was distilled over a 10 cm Vigreux column

Sources & evidence

ORD record
ord-6b6b4d1f4eac4a8c898806dd0317d33e
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Linked notes

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