Pyridine → HCID 18358869, compound

HRID 1954756Notes

Reaction equation

HRID 1954756 reaction equation
N1C=CC=CC=1.[C:7]1([C:13]2[C:17]([CH:18]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[N+:27]([O-:29])=[O:28])[OH:19])=[C:16]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[NH:15][N:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)Cl.[O-2].[O-2].[O-2].[Cr+6]>[C:7]1([C:13]2[C:17]([C:18](=[O:19])[C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=3[N+:27]([O-:29])=[O:28])=[C:16]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[NH:15][N:14]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 1049PyridineHCID 18358879Ethyl 3-phenyl-4-[(4-chloro-2-nitrophenyl)(hydroxy)methyl]-1H-pyrazole-5-carboxylate

Product 1

HCID 18358869HCID 18358869, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of dry pyridine (0.237 g, 300 mmol) in anhydrous methylene chloride (5 mL) was slowly added chromium trioxide (0.15 g, 1.5 mmol) to give a wine colored mixture which was stirred at room temperature for 10 minutes. A solution of ethyl 3-phenyl4[(4-chloro-2-nitrophenyl)-(hydroxy)methyl]-1H-pyrazole-5-carboxylate (0.10 g, 0.25 mmol) in anhydrous methylene chloride (2 mL) was added to the wine red mixture in three portions over 25 minutes. The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was filtered and the filtrate extracted with 3×20 mL 3N HCl. The combined organic extracts were dried with sodium sulfate and concentrated via rotary evaporation to give an oil (0.1 g) which was triturated with hexane:ethyl acetate (4:1) to give the title compound as a tan solid (0.075 g, 75%).

Workup

  1. customto give a wine colored mixture which
  2. stirringThe reaction mixture was stirred at room temperature for 18 hours
  3. filtrationThe reaction mixture was filtered
  4. extractionthe filtrate extracted with 3×20 mL 3N HCl
  5. dry with materialThe combined organic extracts were dried with sodium sulfate
  6. concentrationconcentrated via rotary evaporation

Sources & evidence

ORD record
ord-93bf8ee548bd482399c1a01f579608c7
Source dataset
uspto-grants-2000_09
Patent number
US06124281

Reaction notes

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