Acetic Anhydride → HCID 9797282, compound

HRID 1582697Notes

Reaction equation

HRID 1582697 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:19]=[CH:18][NH:17][N:16]=3)=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:22](OC(=O)C)(=[O:24])[CH3:23]>N1C=CC=CC=1.C(OCC)(=O)C>[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:19]=[CH:18][N:17]([C:22](=[O:24])[CH3:23])[N:16]=3)=[CH:13][CH:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 178526692HCID 178526692, compound

Product 1

HCID 9797282HCID 9797282, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-[4-(-4-nitrophenoxy)phenyl]-1H-pyrazole (0.16 g, 0.57 mmol) in pyridine (12 mL) was treated with neat acetic anhydride (1.0 mL, 1.0 mmol) and allowed to stir at room temperature for 16 hours. The reaction was then diluted with ethyl acetate, washed several times with an aqueous 2N HCl solution, dried over sodium sulfate, and evaporated under reduced pressure. The crude product was purified by column chromatography, affording 116 mg (63%) of the title compound. TLC Rf 0.78 (70:30 hexane/ethyl acetate). 1H NMR (CDCl3): δ 8 8.31 (d, J=3.0 Hz, 1H), 8.22 (d, J=9.3 Hz, 2H), 7.94 (d, J=8.7 Hz, 2H), 7.17 (d, J=9.0 Hz, 2H), 7.07 (d, J=9.3 Hz, 2H), 6.77 (d, J=3.0 Hz, 1H), 2.78 (s, 3H).

Workup

  1. washwashed several times with an aqueous 2N HCl solution
  2. dry with materialdried over sodium sulfate
  3. customevaporated under reduced pressure
  4. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-0e09eec628d74d1194530da0711d956a
Source dataset
uspto-grants-2004_05
Patent number
US06737418B2

Reaction notes

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