Hydrazinium chloride → HCID 178426391, compound

HRID 1624054Notes

Reaction equation

HRID 1624054 reaction equation
[ClH:1].[NH2:2]N.C[N:5](/[CH:7]=[C:8]1/[CH:9]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][C:18]=2[CH3:25])[CH2:10][CH2:11][C:12]([CH3:16])([CH3:15])[C:13]/1=O)C>C(O)C.C(O)(=O)C>[ClH:1].[CH3:15][C:12]1([CH3:16])[C:13]2[C:8](=[CH:7][NH:5][N:2]=2)[CH:9]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][C:18]=2[CH3:25])[CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 115031Hydrazinium chlorideHCID 71114823HCID 71114823, compound

Product 1

HCID 178426391HCID 178426391, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Hydrazine hydrochloride (0.14 g, 2 mmol) is added to 4-[(2Z)-2-(dimethylaminomethylene)-4,4-dimethyl-3-oxo-cyclohexyl]-3-methyl-benzonitrile (0.2 g, 0.67 mmol) in ethanol (30 mL), then acetic acid (two drops) is added to the mixture. After the addition is complete, the reaction mixture is stirred at 80° C. for 3 h. The mixture is cooled to room temperature and concentrated in vacuo. The residue is diluted with ethyl acetate (50 mL) and saturated sodium bicarbonate solution (50 mL). The organic phase is separated and the aqueous phase extracted with ethyl acetate (3×50 mL). The combined organic phase is washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue is purified by silica gel column chromatography (eluted with pet ether:EtOAc=2:1 to 1:1) to give the title compound. The product is added to HCl/ethyl acetate and concentrated in vacuo to give the HCl salt of the title compound (0.12 g, 67%). ES/MS 266 (M+H).

Workup

  1. additionAfter the addition
  2. temperatureThe mixture is cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. additionThe residue is diluted with ethyl acetate (50 mL) and saturated sodium bicarbonate solution (50 mL)
  5. customThe organic phase is separated
  6. extractionthe aqueous phase extracted with ethyl acetate (3×50 mL)
  7. washThe combined organic phase is washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue is purified by silica gel column chromatography (eluted with pet ether:EtOAc=2:1 to 1:1)

Sources & evidence

ORD record
ord-67a5d19738b74ac090cffd9b7865c43f
Source dataset
uspto-grants-2014_07
Patent number
US08778984B2

Reaction notes

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