Hydrazine, dihydrochloride → HCID 178496107, compound

HRID 253250

Reaction equation

HRID 253250 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:17]([C:20](=O)[CH3:21])[C:18]#[N:19])[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][O:15][CH3:16].Cl.Cl.[NH2:25][NH2:26].C(=O)(O)[O-].[Na+]>C(O)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:17]2[C:20]([CH3:21])=[N:25][NH:26][C:18]=2[NH2:19])[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][O:15][CH3:16]

Participants

5

Reactant 3

HCID 17548Hydrazine, dihydrochlorideHCID 516892Sodium BicarbonateHCID 668909162-(3,4-Bis{[2-(methyloxy)ethyl]oxy}phenyl)-3-oxobutanenitrile

Product 1

HCID 178496107HCID 178496107, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(3,4-bis{[2-(methyloxy)ethyl]oxy}phenyl)-3-oxobutanenitrile (0.57 g, 1.9 mmol) in ethanol (5 mL) was added hydrazine dihydrochloride (0.20 g, 2.2 mmol) The resulting mixture was heated at reflux for 1 hour. It was cooled, pour into a saturated sodium bicarbonate solution (10 mL), and the mixture was extracted with ethyl acetate (3×10 mL). The combined extract was washed with aqueous sodium bicarbonate solution, brine, dried over sodium sulfate, filtered and concentrated to give an oily residue which was purified by flash chromatography (silica gel, 5% methanol-dichloromethane) to provide 4-(3,4-bis{[2-(methyloxy)ethyl]oxy}phenyl)-3-methyl-1H-pyrazol-5-amine (0.46 g, 1.4 mmol, 74% yield). 1H NMR (400 MHz, CDCl3): 6.96-6.92 (m, 2H), 6.87-6.84 (d, d, 1H), 4.19-4.16 (m, 4H), 3.79-3.76 (m, 4H), 3.67 (s, 2H), 3.46 (s, 3H), 3.44 (s, 3H), 2.25 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. temperatureIt was cooled
  4. extractionthe mixture was extracted with ethyl acetate (3×10 mL)
  5. extractionThe combined extract
  6. washwas washed with aqueous sodium bicarbonate solution, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give an oily residue which
  11. customwas purified by flash chromatography (silica gel, 5% methanol-dichloromethane)

Sources & evidence

ORD record
ord-6c4ac2695bbe47ee837fa085a8e1b589
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Linked notes

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