Acetic Anhydride → HCID 59834364, compound

HRID 230141Notes

Reaction equation

HRID 230141 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:10]=[C:9]([NH:11][C:12](=[O:14])[CH3:13])[C:8]([CH3:15])=[CH:7][N:6]=1.C(OC(=O)C)(=O)C.C([O-])(=O)C.[K+].[N:33](OCCC(C)C)=O.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1.C(O)(=O)C>[F:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[N:6]=[CH:7][C:8]2[CH:15]=[N:33][N:11]([C:12](=[O:14])[CH3:13])[C:9]=2[CH:10]=1

Participants

8

Reactant 5

HCID 7918Acetic AnhydrideHCID 8053Isoamyl NitriteHCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 59834294HCID 59834294, compound

Product 1

HCID 59834364HCID 59834364, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 241BenzeneSolvent2×

Procedure

A mixture of N-[2-(2,4-difluorophenoxy)-5-methylpyridin-4-yl]acetamide (2.3 g), acetic anhydride (2.6 g), acetic acid (2.7 mL) and potassium acetate (1.7 g) in 40 mL of benzene was brought to reflux. A solution of isoamyl nitrite (1.5 mL) in 10 mL of benzene was added to the refluxing solution over a period of two hours and refluxing was continued for an additional 18 hours. The reaction mixture was cooled and stirred with 50 mL of a 5% aqueous sodium carbonate solution for 3 hours. The organic layer was separated, dried, concentrated and purified via chromatography (silica gel, 8% ethyl acetate/hexane) to give 0.27 g of 1-[6-(2,4-difluorophenoxy)pyrazolo[4,3-c]pyridine-1-yl]ethanone (11% yield). Mass Spec. M+H=290.

Workup

  1. temperatureto reflux
  2. temperaturerefluxing
  3. temperatureThe reaction mixture was cooled
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated
  7. custompurified via chromatography (silica gel, 8% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5e6d6501f8f441a8a2b7e5bb6c9a3c5d
Source dataset
uspto-grants-2009_07
Patent number
US07566708B2

Reaction notes

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