Pyridine → HCID 18358869, compound

HRID 428442Notes

Reaction equation

HRID 428442 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-phenyl-4-[(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-cfd533e4912641b389b42be685c783f9
Source dataset
uspto-grants-2001_11
Patent number
US06313290B1

Reaction notes

Loading…