Hydrochloric Acid → HCID 13921211, compound

HRID 580269Notes

Reaction equation

HRID 580269 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:13]1[C:17]([CH3:18])=[C:16]([N+:19]([O-])=O)[C:15]([CH3:22])=[N:14]1.Cl.[OH-].[Na+].C1(C)C=CC=CC=1>O.[Fe]>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:13]1[C:17]([CH3:18])=[C:16]([NH2:19])[C:15]([CH3:22])=[N:14]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 14798Sodium HydroxideHCID 13921185HCID 13921185, compound

Product 1

HCID 13921211HCID 13921211, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

1-(2-fluoro-4-chloro-5-isopropoxyphenyl)-3,5-dimethyl-4-nitropyrazole (32.8 g) and metallic iron (33.5 g) were suspended in water (140 ml), and the resultant suspension was heated at 80° C., to which 35% aqueous hydrochloric acid (3.2 g) was then added dropwise. After the completion of addition, the reaction mixture was stirred for further 30 minutes at 80° C. Subsequent to cooling, the reaction mixture was brought to pH 9 with aqueous sodium hydroxide solution, followed by addition of toluene to form two layers. The organic layer as separated was washed with water and dried over anhydrous sodium sulfate. Removal of the solvent by distillation in vacuo gave the titled compound (27.7 g) as a pale yellow oil which soon crystallized on standing at room temperature. Recrystallization from a mixture of n-hexane/ethyl acetate yielded a white crystalline solid. m.p. 94°-96.5° C.

Workup

  1. additionwas then added dropwise
  2. additionAfter the completion of addition
  3. temperatureSubsequent to cooling
  4. customto form two layers
  5. customThe organic layer as separated
  6. washwas washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customRemoval of the solvent
  9. distillationby distillation in vacuo

Sources & evidence

ORD record
ord-b116174bed1c40408946c8e5f996db69
Source dataset
uspto-grants-1988_06
Patent number
US04752326

Reaction notes

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