Water → 1-(2-Methylphenyl)-1H-pyrazole

HRID 2198759Notes

Reaction equation

HRID 2198759 reaction equation
O.Cl.[C:3]1([CH3:11])[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH2:10].O.C(O[CH:16](OCC)[CH2:17][CH:18](OCC)OCC)C>C(O)C>[C:3]1([CH3:11])[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH:18]=[CH:17][CH:16]=[N:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 671471,1,3,3-TetraethoxypropaneHCID 20518352(2-Methylphenyl)hydrazine--hydrogen chloride--water (1/1/1)

Product 1

HCID 130663271-(2-Methylphenyl)-1H-pyrazoleYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 1 liter, 2-neck flask, fitted with a condenser and a magnetic stirrer, is successively added 90.0 g. (0.570 M.) of o-tolyl-hydrazine hydrochloride hydrate, 100 ml. of water, 63 ml. of 100% ethanol and 139.0 g. (0.633 M.) of 1,1,3,3-tetraethoxypropane. The reaction mixture is then heated slowly to between 80° C. and 90° C., and after maintaining the mixture at this temperature range for a period of about 3 hours, the reaction mixture is quenched on ice water and extracted with ethylacetate/ether. After drying the organic solution over anhydrous sodium sulfate, the solvents are evaporated to obtain a very dark liquid. Distillation in an air oven at a temperature between 110°-120° C. and a pressure of 1 mm. of Hg. yielded a light yellow oil (Yield: 83%).

Workup

  1. customInto a 1 liter, 2-neck flask, fitted with a condenser and a magnetic stirrer
  2. temperatureThe reaction mixture is then heated slowly to between 80° C. and 90° C.
  3. temperatureafter maintaining the mixture at this temperature range for a period of about 3 hours
  4. customthe reaction mixture is quenched on ice water
  5. extractionextracted with ethylacetate/ether
  6. dry with materialAfter drying the organic solution over anhydrous sodium sulfate
  7. customthe solvents are evaporated
  8. customto obtain a very dark liquid
  9. distillationDistillation in an air oven at a temperature between 110°-120° C.

Sources & evidence

ORD record
ord-bda564a2a28a4932afb3fa92ee2644de
Source dataset
uspto-grants-1982_11
Patent number
US04359474

Reaction notes

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