Acetic Anhydride → HCID 15277998, compound

HRID 1463190Notes

Reaction equation

HRID 1463190 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH3:13])[C:8]([CH3:12])=[N:9][C:10]=1[CH3:11])(=[O:3])[CH3:2].C(OC(=O)C)(=O)C.C([O-])(=O)C.[K+].[N:26](OCCCCC)=O.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1.C(O)(=O)C>[C:1]([N:4]1[C:5]2[C:10](=[N:9][C:8]([CH3:12])=[C:7]([CH3:13])[CH:6]=2)[CH:11]=[N:26]1)(=[O:3])[CH3:2]

Participants

8

Reactant 5

HCID 7918Acetic AnhydrideHCID 10026Pentyl nitriteHCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 15277997HCID 15277997, compound

Product 1

HCID 15277998HCID 15277998, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 241BenzeneSolvent2×

Procedure

The reaction was run similar to that described by D. Chapman and J. Durst, J. Chem. Soc. Perkin I, 2398 (I980). A 12.40 g sample of the 5-(acetylamino)-2,3,6-trimethylpyridine was combined with 22 mL of acetic anhydride, 22 mL of acetic acid, and 13 g of potassium acetate in 200 mL of benzene. The mixture was brought to relux. A solution of an excess of amyl nitrite, (11 g) in benzene (40 mL), was added to the refluxing solution over a period of 2 hours and refluxing was continued an additional 12 hours. The reaction was cooled and stirred, with 200 mL of 5% aqueous sodium carbonate, for 3 hours. The organic phase was separated, dried with anhydrous sodium sulfate, concentrated under vacuum and chromatographed (silica gel: methylene chloride/ether) to give 4.94 g of 1-acetyl-5,6-dimethylpyrazolo [4,3-b] pyridine. ##STR6##

Workup

  1. temperaturerefluxing
  2. temperatureThe reaction was cooled
  3. customThe organic phase was separated
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customchromatographed (silica gel: methylene chloride/ether)

Sources & evidence

ORD record
ord-9587e46b86f449de9ee136e5747e04d1
Source dataset
uspto-grants-1994_04
Patent number
US05300478

Reaction notes

Loading…