Hydrochloric Acid → HCID 13769128, compound

HRID 978933Notes

Reaction equation

HRID 978933 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N:11]2[C:15]([Cl:16])=[C:14]([Br:17])[C:13]([CH3:18])=[N:12]2)=[C:4]([F:19])[CH:3]=1.C(O)C.Cl>[Fe].O>[NH2:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([F:19])=[C:5]([N:11]2[C:15]([Cl:16])=[C:14]([Br:17])[C:13]([CH3:18])=[N:12]2)[CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 13769112HCID 13769112, compound

Product 1

HCID 13769128HCID 13769128, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

12.5 g (0.034 mol) of 1-(4-chloro-2-fluoro-5-nitrophenyl)-3-methyl-4-bromo-5-chloropyrazole (reference example 2) were added in the solution of 13.6 g of iron powder, 44 ml of ethanol, 20 ml of water and 0.2 ml of hydrochloric acid at 70° to 75° C., under stirring. After stirred for 2 hours at 75° C., the reaction mixture was filtered and the filtrate added with cold water was extracted with ethyl acetate. The ester layer was washed with water, concentrated and purified on column chromatography to obtain 11.0 g of brown crystal, melting point: 113° to 116° C. in yield of 96%.

Workup

  1. stirringAfter stirred for 2 hours at 75° C.
  2. filtrationthe reaction mixture was filtered
  3. additionthe filtrate added with cold water
  4. extractionwas extracted with ethyl acetate
  5. washThe ester layer was washed with water
  6. concentrationconcentrated
  7. custompurified on column chromatography

Sources & evidence

ORD record
ord-8bd5dc43e51440d7978f94c6ed68bb21
Source dataset
uspto-grants-1987_05
Patent number
US04666507

Reaction notes

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