HCID 53778256, compound → HCID 178507596, compound

HRID 982167Notes

Reaction equation

HRID 982167 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[C:5]([Cl:10])=[C:4]([Cl:11])[C:3]=1[N:12]1[C:16](=[O:17])[CH2:15][C:14]([NH:18][C:19]2[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:20]=2[Cl:28])=[N:13]1.[N+](C1C(=O)N=NC=1)([O-])=O>FC(F)(F)C(O)=O.[Fe]>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[C:5]([Cl:10])=[C:4]([Cl:11])[C:3]=1[N:12]1[C:16](=[O:17])[CH2:15][C:14]([NH:18][C:19]2[CH:24]=[C:23]([NH2:25])[CH:22]=[CH:21][C:20]=2[Cl:28])=[N:13]1

Participants

5

Reactant 2

HCID 53778256HCID 53778256, compoundHCID 178516452HCID 178516452, compound

Product 1

HCID 178507596HCID 178507596, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

Iron powder (3.5 g) was added in portions over five minutes to a slurry of 1-(2,3,4,5,6-pentachlorophenyl)-3-(2'-chloro-5'-nitroanilino)-2-pyrazoline-5-one (5 g) in trifluoroacetic acid (50 ml) at 70° C. The yellow color of the nitropyrazolone rapidly disappeared, and after stirring at 70°-75° C. for ten minutes the hot solution was separated from any unreacted iron and added to stirred ice-water (400 ml). The resultant off-white precipitate of the aminopyrazolone was filtered off, washed with water and dried. The yield was 4.6 g (98%); single spot by thin layer chromatography.

Workup

  1. customwas separated from any unreacted iron
  2. additionadded
  3. stirringto stirred ice-water (400 ml)
  4. filtrationThe resultant off-white precipitate of the aminopyrazolone was filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-5f9ec4f9a32e4305bf333958787bcc62
Source dataset
uspto-grants-1991_02
Patent number
US04994576

Reaction notes

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