Ammonia → HCID 20322978, compound

HRID 839476Notes

Reaction equation

HRID 839476 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[CH2:13][C:12]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:25](OCC)(=[O:27])[CH3:26].O.N>C(OC(=O)C)(=O)C.[Cl-].[Zn+2].[Cl-]>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14](=[O:15])[CH2:13][C:12]([N:16]([C:25](=[O:27])[CH3:26])[C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[N:11]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 8857Ethyl Acetate2×HCID 178492220HCID 178492220, compound

Product 1

HCID 20322978HCID 20322978, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 7918Acetic AnhydrideSolvent2×

Conditions

Temperature
5 °C

Procedure

32.6 g of 1-(4-nitrophenyl)-3-(4-methoxyanilino)-5-oxo-2-pyrazoline was dispersed in 110 g of acetic anhydride and 2.7 g of zinc chloride was added thereto and heated (70° to 80° C) on a steam bath with stirring. The mixture became a uniform solution as the reaction proceeded. After the completion of the reaction, 500 ml of ethyl acetate and 500 ml of water were added the reaction mixture and concentrated aqueous ammonia (28%) was added dropwise thereto under cooling to completely decompose the excess acetic anhydride. The crystals deposited in the ethyl acetate were collected by filtration. The filtrate was sufficiently washed with water and the ethyl acetate solution was concentrated to one-third of its original volume and cooled (5° C) to yield a second amount of crystals which was added to the first crystals obtained. Total yield of the product was 31 g. The melting point was 165° to 167° C.

Workup

  1. temperatureheated (70° to 80° C) on a steam bath
  2. additionwas added dropwise
  3. temperatureunder cooling
  4. filtrationwere collected by filtration
  5. washThe filtrate was sufficiently washed with water
  6. concentrationthe ethyl acetate solution was concentrated to one-third of its original volume
  7. customto yield a second amount of crystals which
  8. additionwas added to the first crystals
  9. customobtained

Sources & evidence

ORD record
ord-f6fc60ab4b8e462da4cf9777c073b870
Source dataset
uspto-grants-1978_06
Patent number
US04095984

Reaction notes

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