1,1-Dimethylhydrazine → HCID 69788456, compound

HRID 488731Notes

Reaction equation

HRID 488731 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1.[CH3:17][N:18]([CH3:20])[NH2:19]>CCO>[CH3:17][N:18]([CH3:20])[N:19]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 59761,1-DimethylhydrazineHCID 221478034-[(2-Oxocyclohexyl)methyl]benzonitrile

Product 1

HCID 69788456HCID 69788456, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-[(2-oxocyclohexyl)methyl]-benzonitrile (7 g) (0.033 mol) and anhydrous N,N-dimethylhydrazine (9.2 ml) (3,7 eq.) in EtOH (100 ml) was refluxed for 8 h. After cooling, the reaction mixture was concentrated to dryness. The residue was partitioned between tBuOMe and water, the organic phase washed twice with water, dried over magnesium sulfate, and concentrated to yield 4-[[2-(dimethylhydrazono)cyclohexyl]methyl]-benzonitrile (6.1 g) as a orange oil. 1H NMR (CDCl3): 7.55 (2H, d), 7.30 (2H, d), 3.15 (1H, dd), 2.9-2.15 (6H, m), 2.3 (6H, s), 1.8-1.3 (4H, m).

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated to dryness
  3. customThe residue was partitioned between tBuOMe and water
  4. washthe organic phase washed twice with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f525c20d24d64e5e95d767d918cb9828
Source dataset
uspto-grants-2005_12
Patent number
US06974815B2

Reaction notes

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