Ethylene Glycol → HCID 178494456, compound

HRID 1659438Notes

Reaction equation

HRID 1659438 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH2:13][C:12](=O)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.Cl.Cl.[NH2:17][NH2:18].NN.C(O)CO>O>[NH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[C:12]1[NH:18][N:17]=[C:4]([CH2:3][O:2][CH3:1])[CH:13]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 9321HydrazineHCID 17548Hydrazine, dihydrochlorideHCID 67788818HCID 67788818, compound

Product 1

HCID 178494456HCID 178494456, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7.5 g (0.04 mol) of 2-methoxymethyl-4-quinolone, 4.2 g (0.04 mol) of hydrazine dihydrochloride, 12.8 ml (0.4 mol) of 95% hydrazine and 30 ml of ethylene glycol is slowly heated to reflux. The resulting solution is refluxed for 5 hours, cooled, diluted with 200 ml of distilled water, and extracted twice with methylene chloride (1×400 ml, 1×200 ml). The combined methylene chloride extracts are washed with 100 ml of distilled water, dried over sodium sulfate, and evaporated to 8.0 g of clear oil. Trituration with 25 ml of hexane gives 6.95 g (86%) of the 5-(2-aminophenyl)-3-methoxymethylpyrazole as a white powder, m.p. 74.0-78.0° C.

Workup

  1. temperatureis slowly heated to reflux
  2. temperatureThe resulting solution is refluxed for 5 hours
  3. temperaturecooled
  4. extractionextracted twice with methylene chloride (1×400 ml, 1×200 ml)
  5. washThe combined methylene chloride extracts are washed with 100 ml of distilled water
  6. dry with materialdried over sodium sulfate
  7. customevaporated to 8.0 g of clear oil

Sources & evidence

ORD record
ord-413879c732ea49048c48f056fb8e4835
Source dataset
uspto-grants-1981_12
Patent number
US04303795

Reaction notes

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