Sodium Hydroxide → 2-(3,4-dichlorophenyl)-N-methyl-3,4-dihydropyrazol-5-amine

HRID 544282Notes

Reaction equation

HRID 544282 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([N:15]2[CH2:19][CH:18]=[C:17]([NH:20][CH:21]=O)[NH:16]2)[CH:11]=[CH:12][C:13]=1[Cl:14].[H-].[OH-].[Na+].[Si]([O-])([O-])([O-])[O-].[Mg+2].[Mg+2]>ClCCl.CCOCC.O.O1CCCC1>[Cl:7][C:8]1[CH:9]=[C:10]([N:15]2[CH2:19][CH2:18][C:17]([NH:20][CH3:21])=[N:16]2)[CH:11]=[CH:12][C:13]=1[Cl:14]

Participants

10

Reactant 5

HCID 14798Sodium HydroxideHCID 66225Magnesium orthosilicate2×HCID 166653HydrideHCID 20459963N-[1-(3,4-dichlorophenyl)-3-pyrazolin-3-yl]formamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 1784824892-(3,4-dichlorophenyl)-N-methyl-3,4-dihydropyrazol-5-amine

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 250 ml. of freshly distilled tetrahydrofuran under nitrogen is added cautiously 5.0 g. of lithium aluminum hydride, then 5.0 g. of N-[1-(3,4-dichlorophenyl)-3-pyrazolin-3-yl]formamide is added portionwise and the mixture is refluxed under nitrogen for 6 hours. The reaction mixture is cooled and the excess hydride is decomposed by the cautious dropwise addition of 5.0 ml. of water followed by 5.0 ml. of 15% sodium hydroxide solution and 15 ml. of water. The mixture is filtered and the filtrate is evaporated to give a gum and solid. This material is dissolved in dichloromethane and passed through a short column of a hydrous magnesium silicate. The effluent is evaporated to give a dark gum and solid. The mixture is dissolved in ether and treated as above with a hydrous magnesium silicate. The effluent is evaporated and the solid is recrystallized twice from ether-hexane to give 2.0 g. of the desired product as white crystals, m.p. 68°-70° C.

Workup

  1. temperaturethe mixture is refluxed under nitrogen for 6 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationThe mixture is filtered
  4. customthe filtrate is evaporated
  5. customto give a gum and solid
  6. customThe effluent is evaporated
  7. customto give a dark gum and solid
  8. customThe effluent is evaporated
  9. customthe solid is recrystallized twice from ether-hexane
  10. customto give 2.0 g

Sources & evidence

ORD record
ord-ce40365f92d841e29baceed8394e3c11
Source dataset
uspto-grants-1984_05
Patent number
US04448973

Reaction notes

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