Hydrochloric Acid → HCID 178470425, compound

HRID 428436Notes

Reaction equation

HRID 428436 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[C:9]([C:18]([F:21])([F:20])[F:19])=[N:10][NH:11][C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])=[C:4]([N+:24]([O-])=O)[CH:3]=1.Cl.O>C(O)C.B#[Ni]>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[C:9]([C:18]([F:21])([F:19])[F:20])=[N:10][NH:11][C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])=[C:4]([NH2:24])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 178470426HCID 178470426, compound

Product 1

HCID 178470425HCID 178470425, compoundYield 104%

Reagents, catalysts & solvents 2

HCID 82791nickel boride (NiB)CatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

The freshly prepared nickel boride (1.06 g) was added to a solution of ethyl 4-(4-chloro-2-nitrobenzoyl)-3-trifluoromethyl-1H-pyrazole-5-carboxylate (437.0 mg, 1.116 mmol) in ethanol (20 mL) followed by addition of 1.0 N aqueous hydrochloric acid (5.0 mL). This mixture was stirred at 60° C. for 30 minutes and then at room temperature overnight (17 hours). The reaction mixture was poured into water (250 mL) and extracted with diethyl ether (2×250 mL). The organic extract was filtered to remove residual black solids, washed successively with water (250 mL) and saturated aqueous sodium chloride (250 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated by rotary evaporation to afford 0.42 g of greenish-yellow solid. This material was dissolved in ethyl acetate (50 mL) and preabsorbed onto 4.1 g of silica gel, which was then applied to the top of a 40 g (2.84×14.2 cm) silica gel flash chromatography column. The column was eluted with hexane-ethyl acetate (90:10 then 80:20) to give 235.6 mg (58.4%) of the title compound as a light yellow solid.

Workup

  1. customat room temperature
  2. customovernight (17 hours)
  3. extractionextracted with diethyl ether (2×250 mL)
  4. extractionThe organic extract
  5. filtrationwas filtered
  6. customto remove residual black solids
  7. washwashed successively with water (250 mL) and saturated aqueous sodium chloride (250 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-18848fc39f9e48feb951490616fedc54
Source dataset
uspto-grants-2001_11
Patent number
US06313290B1

Reaction notes

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