Hydrazine hydrate (1:1) → HCID 18355415, compound

HRID 429320Notes

Reaction equation

HRID 429320 reaction equation
[Cl:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[N:4]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[C:19]([O:26][CH3:27])[CH:18]=2)[N:3]=1.O.NN>C(O)C.O1CCCC1>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([N:4]2[C:5]([C:7]3[CH:8]=[CH:9][C:10]([S:13]([CH3:16])(=[O:14])=[O:15])=[CH:11][CH:12]=3)=[CH:6][C:2]([Cl:1])=[N:3]2)=[CH:18][C:19]=1[O:26][CH3:27]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 18355378HCID 18355378, compound

Product 1

HCID 18355415HCID 18355415, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-chloro-1-(3-methoxy-4-nitrophenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole (900 mg) in ethanol (30 ml) and tetrahydrofuran (30 ml) were added active carbon (3 g), hydrazine monohydrate (2 ml) and ferric chloride (50 mg). The mixture was refluxed for 2 hours, and filtered. The filtrate was evaporated in vacuo and partitioned between water and dichloromethane. The organic layer was dried over magnesium sulfate and filtered. The filtrate was evaporated in vacuo to give 1-(4-amino-3-methoxyphenyl)-3-chloro-5-[4-(methylsulfonyl)phenyl]pyrazole (820 mg).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. filtrationfiltered
  3. customThe filtrate was evaporated in vacuo
  4. custompartitioned between water and dichloromethane
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-4461e16a87b644a39cecfdd238e4714a
Source dataset
uspto-grants-2001_11
Patent number
US06316485B1

Reaction notes

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