Pyridine → HCID 53666718, compound

HRID 342952Notes

Reaction equation

HRID 342952 reaction equation
[OH:1][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22])[C:3]1[CH:4]=[N:5][O:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1.[C:24](Cl)(=[O:26])[CH3:25].N1C=CC=CC=1>ClCCl>[C:24]([O:1][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:20])[F:19])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22])[C:3]1[CH:4]=[N:5][O:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 54050151HCID 54050151, compound

Product 1

HCID 53666718HCID 53666718, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-[hydroxy-(2-nitro-4-trifluoromethylphenyl)methyl]-5-cyclopropylisoxazole (0.69 g), acetyl chloride (0.27 g) and pyridine (0.10 g) in dichloromethane (40 ml) was stirred at 0° C. for 4 hours. The mixture was quenched with water and extracted with dichloromethane. The organic extracts were dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness. The residue was triturated with ether/petroleum ether to give 4-[acetoxy-(2-nitro-4-trifluoromethylphenyl)methyl]-5-cyclopropylisoxazole (compound 297, 0.46 g) as a yellow solid: m.p. 82° C.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic extracts were dried (anhydrous magnesium sulphate)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customThe residue was triturated with ether/petroleum ether

Sources & evidence

ORD record
ord-cbdaa42eeff54f8b88972f2327315a40
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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