Hydrochloric Acid → HCID 18943173, compound

HRID 400090Notes

Reaction equation

HRID 400090 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:9]([NH:11][C:12]1[CH:13]=[C:14]([CH:21]=[CH:22][CH:23]=1)[CH:15]=[CH:16][C:17](OC)=[O:18])=[O:10].C[O-].[Na+].Cl>O.C(#N)C.CO>[C:1]1([N:7]2[CH:15]([C:14]3[CH:21]=[CH:22][CH:23]=[C:12]([NH:11][CH:9]=[O:10])[CH:13]=3)[CH2:16][C:17](=[O:18])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7516PhenylhydrazineHCID 10942334Sodium MethoxideHCID 54484240Methyl 3-formamidocinnamate

Product 1

HCID 18943173HCID 18943173, compoundYield 35.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

108 g of phenylhydrazine, 205 g of methyl 3-formamidocinnamate, 200 ml of a 28% methanol solution of sodium methoxide and 400 ml of acetonitrile were mixed and heated under reflux for 1 hour in a nitrogen stream. 2 of the reaction solution was poured into water and 100 ml of concentrated hydrochloric acid was added. Then, precipitate was produced. The precipitate was collected by filtration and recrystallized from acetonitrile to obtain 99 g of 1-phenyl-5-(3-formamidophenyl) pyrazolidin-3-one as white crystals.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour in a nitrogen stream
  3. additionwas added
  4. customThen, precipitate was produced
  5. filtrationThe precipitate was collected by filtration
  6. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-247d8d3c4f974f05864e2f1b754644a5
Source dataset
uspto-grants-1998_10
Patent number
US05827638

Reaction notes

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