Sodium Hydroxide → 4-chlorophenyl-4-methyl-4,5-dihydro-1H-pyrazole

HRID 1607207Notes

Reaction equation

HRID 1607207 reaction equation
CN(C)CC(C)C([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)=O.O.NN.[OH-].[Na+].ClC1C=CC([C:28]2[CH:32]([CH3:33])[CH2:31][NH:30][N:29]=2)=CC=1>C(O)CC>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([N:30]2[CH2:31][CH:32]([CH3:33])[CH:28]=[N:29]2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 124144373-Dimethylamino-2-methyl-4'-chloropropiophenoneHCID 137525563-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole

Product 1

HCID 544104994-chlorophenyl-4-methyl-4,5-dihydro-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

In a 500 ml round bottomed flask equipped with a reflux condensor was placed 100 g of 3-dimethylamino-2-methyl-4'-chloropropiophenone (0.47 mole), 200 ml of n-propanol, 48 g of hydrazine monohydrate (0.96 mole), and 5 g of 50% aqueous sodium hydroxide. The mixture was refluxed for 2 hours. The solvent was removed in vacuo and the product was partitioned between methylene chloride and water. The organic layer was washed 3 times with water and dried over anyhdrous magnesium sulfate. The organic layer contains 82 g (0.42 mole) of 3-(4-chlorophenyl)-4-methyl-4,5-dihydro-1H-pyrazole an air sensitive solid. NMR data was consistent with the structure.

Workup

  1. customIn a 500 ml round bottomed flask equipped with a reflux condensor
  2. temperatureThe mixture was refluxed for 2 hours
  3. customThe solvent was removed in vacuo
  4. customthe product was partitioned between methylene chloride and water
  5. washThe organic layer was washed 3 times with water
  6. dry with materialdried over anyhdrous magnesium sulfate

Sources & evidence

ORD record
ord-9ab5de72b6cb42d0be72dc2e399be89d
Source dataset
uspto-grants-1989_09
Patent number
US04863947

Reaction notes

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