Acetic Anhydride → HCID 86593611, compound

HRID 1269838Notes

Reaction equation

HRID 1269838 reaction equation
C(OC(=O)C)(=O)C.C([O-])(=O)C.[K+].[N:13](OCCC(C)C)=O.[CH3:21][S:22]([O:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:35])[CH3:34])=[C:28]([CH3:36])[C:27]=1[O:37][CH3:38])(=[O:24])=[O:23]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.O>[CH3:21][S:22]([O:25][C:26]1[C:27]([O:37][CH3:38])=[C:28]2[C:29](=[CH:30][CH:31]=1)[N:32]([C:33](=[O:35])[CH3:34])[N:13]=[CH:36]2)(=[O:24])=[O:23]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 8053Isoamyl Nitrite2×HCID 517044Potassium AcetateHCID 22933738HCID 22933738, compound

Product 1

HCID 86593611HCID 86593611, compoundYield 141.2%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetic anhydride (155?1, 1.65 mmol), tetrabutylammonium bromide (8.8 mg, 0.0274 mmol), potassium acetate (108 mg, 1.10 mmol) and isoamyl nitrite (0.096 ml, 0.274 mmol) were added to a solution of 4-(acetylamino)-2-methoxy-3-methylphenyl methanesulfonate (150 mg, 0.549 mmol) in ethyl acetate (1.5 ml) at room temperature. After 8 hours, isoamyl nitrite (0.037 ml, 0.713 mmol) was further added thereto. After another 2 hours, the mixture thus obtained was poured into water (20 ml) and extracted with ethyl acetate (20 ml×2), and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 1-acetyl-4-methoxy-1H-indazol-5-yl methanesulfonate (110 mg, 70%).

Workup

  1. waitAfter another 2 hours
  2. customthe mixture thus obtained
  3. extractionextracted with ethyl acetate (20 ml×2)
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. customThe organic layer dried
  6. concentrationwas concentrated under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1a6ee5da809b4fb582cdb8c278305203
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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