Hydrazinium chloride → HCID 86674930, compound

HRID 1624047Notes

Reaction equation

HRID 1624047 reaction equation
C[N:2](/[CH:4]=[C:5]1/[CH:6]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[CH2:7][C:8]([CH3:12])([CH3:11])[C:9]/1=O)C.[ClH:21].[NH2:22]N>C(O)C.C(O)(=O)C>[ClH:21].[CH3:11][C:8]1([CH3:12])[C:9]2[NH:22][N:2]=[CH:4][C:5]=2[CH:6]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[CH2:7]1

Participants

5

Reactant 2

HCID 115031Hydrazinium chlorideHCID 86674931HCID 86674931, compound

Product 1

HCID 86674930HCID 86674930, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To (+/−)-4-[(2Z)-2-(dimethylaminomethylene)-4,4-dimethyl-3-oxo-cyclopentyl]benzonitrile (3.2 g, 20 mmol) in ethanol (100 mL) and acetic acid (4 drops) is added hydrazine hydrochloride (4.17 g, 60 mmol) and the reaction is heated to 80° C. for three hours. The reaction is then cooled to room temperature and concentrated in vacuo. The residue is partitioned between ethyl acetate and saturated sodium bicarbonate solution. The layers are separated and the organic is washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue is purified by silica gel flash chromatography eluting with 1:2 ethyl acetate:pet ether. The resulting material is treated with HCl in ethyl acetate to provide the title compound (2.3 g, 70%). ES/MS (m/z) 238.2 (M+1).

Workup

  1. temperatureThe reaction is then cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe residue is partitioned between ethyl acetate and saturated sodium bicarbonate solution
  4. customThe layers are separated
  5. washthe organic is washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by silica gel flash chromatography
  10. washeluting with 1:2 ethyl acetate
  11. additionThe resulting material is treated with HCl in ethyl acetate

Sources & evidence

ORD record
ord-6a44a0f587a84de69b4ca58d4c48186f
Source dataset
uspto-grants-2014_07
Patent number
US08778984B2

Reaction notes

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