Hydrazine, dihydrochloride → HCID 178496120、化合物

HRID 253257

反応式

HRID 253257 の反応式
[CH3:1][O:2][C:3]1[C:8]([O:9][CH2:10][CH2:11][O:12][CH3:13])=[CH:7][CH:6]=[CH:5][C:4]=1[CH:14]([C:17](=O)[CH3:18])[C:15]#[N:16].Cl.Cl.[NH2:22][NH2:23].C(=O)(O)[O-].[Na+]>C(O)C>[CH3:18][C:17]1[C:14]([C:4]2[CH:5]=[CH:6][CH:7]=[C:8]([O:9][CH2:10][CH2:11][O:12][CH3:13])[C:3]=2[O:2][CH3:1])=[C:15]([NH2:16])[NH:23][N:22]=1

参加物

5

反応物 3

HCID 17548Hydrazine, dihydrochlorideHCID 516892Sodium BicarbonateHCID 668911252-(2-(Methyloxy)-3-{[2-(methyloxy)ethyl]oxy}phenyl)-3-oxobutanenitrile

生成物 1

HCID 178496120HCID 178496120、化合物収率 65%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 2-(2-(methyloxy)-3-{[2-(methyloxy)ethyl]oxy}phenyl)-3-oxobutanenitrile (0.17 g, 0.65 mmol) in ethanol (5 mL) was added hydrazine dihydrochloride (99 mg, 0.94 mmol). The resulting mixture was heated at reflux for 1 hour. It was cooled, poured 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 in dichloromethane) to provide 3-methyl-4-(2-(methyloxy)-3-{[2-(methyloxy)ethyl]oxy}phenyl)-1H-pyrazol-5-amine (115 mg, 0.42 mmol, 65% yield). MS (EI) for C14H19N3O3: 278 (MH+).

後処理

  1. temperatureThe resulting mixture was 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 in dichloromethane)

出典と根拠

ORDレコード
ord-0c550d25001a4059a57bc31db4a502a6
出典データセット
uspto-grants-2011_01
特許番号
US07872014B2

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