Pyridine → HCID 178470426, compound

HRID 428435Notes

Reaction equation

HRID 428435 reaction equation
N1C=CC=CC=1.[F:7][C:8]([F:32])([F:31])[C:9]1[C:13]([CH:14]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[N+:23]([O-:25])=[O:24])[OH:15])=[C:12]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[NH:11][N:10]=1>ClCCl.[O-2].[Cr+6].[O-2].[O-2]>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]([C:13]2[C:9]([C:8]([F:31])([F:7])[F:32])=[N:10][NH:11][C:12]=2[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:15])=[C:17]([N+:23]([O-:25])=[O:24])[CH:18]=1

Participants

5

Reactant 2

HCID 1049PyridineHCID 178470427HCID 178470427, compound

Product 1

HCID 178470426HCID 178470426, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Chromium(VI) oxide (CrO3, 2.828 g, 28.28 mmol) was added to a solution of pyridine (4.58 mL, 56.63 mmol) in dichloromethane (70 mL) and the mixture was stirred at room temperature for 15 minutes. To the resulting burgundy-colored solution was added a solution of ethyl 3-trifluoromethyl-4-[(4-chloro-2-nitro-phenyl)(hydroxy)methyl]-1H-pyrazole-5-carboxylate (1.64 g, 4.17 mmol) in dichloromethane (15 mL). The resulting mixture was stirred at room temperature for 4 days. The dichloromethane solution was decanted from the dark viscous residue, which was washed with diethyl ether (3×100 mL). The dichloromethane and diethyl ether extracts were combined, washed successively with 1 N aqueous hydrochloric acid (2×100 mL) and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated by rotary evaporation to afford 1.33 g (82%) of the title compound as a yellow solid.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 4 days
  2. customThe dichloromethane solution was decanted from the dark viscous residue, which
  3. washwas washed with diethyl ether (3×100 mL)
  4. washwashed successively with 1 N aqueous hydrochloric acid (2×100 mL) and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-ce4f53a6109144a8aa6ad6b723cb969e
Source dataset
uspto-grants-2001_11
Patent number
US06313290B1

Reaction notes

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