Methylhydrazine → HCID 21441230, compound

HRID 328292Notes

Reaction equation

HRID 328292 reaction equation
[CH3:1][NH:2][NH2:3].[C:4]1([C:10](=O)[CH:11]([CH2:20][CH3:21])[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=O)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)(C)C>[C:4]1([C:10]2[C:11]([CH2:20][CH3:21])=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:2]([CH3:1])[N:3]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 105149681,3-Propanedione, 2-ethyl-1,3-diphenyl-

Product 1

HCID 21441230HCID 21441230, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

Methylhydrazine (2.86 g, 0.06 mole) is added to an isopropanol (100 ml) solution of 1,3-diphenyl-2-ethyl-1,3-propanedione (11.0 g, 0.044 mole) with constant stirring at 80° C. The reaction mixture is heated at reflux for 31/2 hours, then stirred at room temperature overnight. The reaction mixture is poured into ice-water, stirred for 1/2 hour, and the resulting mixture extracted with chloroform (3×50 ml). Evaporation of the organic layer gives an oil, which is crystallized from hexane with cooling to give 6.47 g (56%) of product, m.p. 80° C to 81° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 31/2 hours
  3. stirringstirred at room temperature overnight
  4. stirringstirred for 1/2 hour
  5. extractionthe resulting mixture extracted with chloroform (3×50 ml)
  6. customEvaporation of the organic layer
  7. customgives an oil, which
  8. customis crystallized from hexane
  9. temperaturewith cooling

Sources & evidence

ORD record
ord-ae2e7da478344d4face47c525cefa345
Source dataset
uspto-grants-1977_04
Patent number
US04017298

Reaction notes

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