Sodium Hydroxide → 3-(4-Chlorophenyl)-4,5-dihydro-1H-pyrazole

HRID 12493

Reaction equation

HRID 12493 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][CH2:11][N:12](C)C)=[CH:5][CH:4]=1.O.[NH2:17]N.[OH-].[Na+]>CO>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][NH:12][N:17]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 2003701-Propanone, 1-(4-chlorophenyl)-3-(dimethylamino)-, hydrochloride (1:1)

Product 1

HCID 131437003-(4-Chlorophenyl)-4,5-dihydro-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

Under N2 atmosphere, 1-(4-chloro-phenyl)-3-dimethylamino-propan-1-one hydrochloride (37.2 g) was dissolved in warm MeOH (75 mL), and slowly added to a solution of hydrazine hydrate (23 mL) and 50% aqueous NaOH (12 mL) in MeOH (30 mL) stirred at 50° C. The mixture was refluxed for 2 hours, and evaporated under reduced pressure. Water was added to the residue, followed by extraction with DCM. The organic phase was washed twice with water, dried and evaporated under reduced pressure, to give 25.0 g of a yellow solid, m.p. 90-100° C.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customevaporated under reduced pressure
  3. additionWater was added to the residue
  4. extractionfollowed by extraction with DCM
  5. washThe organic phase was washed twice with water
  6. customdried
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-46422b9f44604933bc9aea30a17a0796
Source dataset
uspto-grants-2010_06
Patent number
US07728018B2

Linked notes

Loading…