Acetic Anhydride → HCID 57585973, compound

HRID 547616Notes

Reaction equation

HRID 547616 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:19]=[CH:18][C:16]([NH2:17])=[C:15]([CH3:20])[CH:14]=2)=[CH:8][CH:7]=1.[C:21]([O-:24])(=O)[CH3:22].[K+].C(OC(=O)C)(=O)C.C(O[N:39]=O)CC(C)C.C1OCCOCCOCCOCCOCCOC1.C([O-])(O)=O.[Na+]>O1CCCC1>[C:21]([N:17]1[C:16]2[C:15](=[CH:14][C:13]([O:12][C:9]3[CH:10]=[CH:11][C:6]([CH:2]4[O:3][CH2:4][CH2:5][O:1]4)=[CH:7][CH:8]=3)=[CH:19][CH:18]=2)[CH:20]=[N:39]1)(=[O:24])[CH3:22]

Participants

8

Reactant 6

HCID 7918Acetic AnhydrideHCID 8053Isoamyl NitriteHCID 2855718-Crown-6HCID 516892Sodium BicarbonateHCID 517044Potassium AcetateHCID 57585850HCID 57585850, compound

Product 1

HCID 57585973HCID 57585973, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-{[4-(1,3-dioxolan-2-yl)phenyl]oxy}-2-methylaniline (1.24 g, 4.55 mmol) in 40 mL tetrahydrofuran at room temperature was treated with potassium acetate (490 mg, 5 mmol) followed by acetic anhydride (1.42 mL, 15 mmol). After 10 minutes, the reaction was treated with isoamylnitrite (0.915 mL, 6.8 mmol) and heated to reflux for 3 hours. Catalytic 18-crown-6 was added and the reaction was refluxed for 4 days. Upon cooling to room temperature, the reaction mixture was poured into saturated aqueous NaHCO3 and extracted with ethylacetate. The organic was rinsed with brine, dried over MgSO4, and concentrated. The crude material was purified via silica gel column chromatography (0% to 100% ethyl acetate in hexane gradient) to provide 0.835 g 1-acetyl-5-{[4-(1,3-dioxolan-2-yl)phenyl]oxy}-1H-indazole.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. temperaturethe reaction was refluxed for 4 days
  4. extractionextracted with ethylacetate
  5. washThe organic was rinsed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe crude material was purified via silica gel column chromatography (0% to 100% ethyl acetate in hexane gradient)

Sources & evidence

ORD record
ord-5a1ff15a6c3d4626a6b5de942c8f3767
Source dataset
uspto-grants-2011_05
Patent number
US07939528B2

Reaction notes

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