Dimethylformamide → HCID 21897597, compound

HRID 852070Notes

Reaction equation

HRID 852070 reaction equation
[OH-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH3:9][N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.[H-].[Na+].[CH3:17][C:18](C)([O-:20])C.[K+].C[N:24]([CH3:27])C=O>[Cu].O.C(O)C.CO.C(O)(C)C>[N:10]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[C:27]1[CH:17]=[CH:18][O:20][N:24]=1

Participants

12

Reactant 6

HCID 6228DimethylformamideHCID 84541-MethylpyrrolidineHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 24758Sodium hydrideHCID 23665647Potassium tert-butoxide

Product 1

HCID 21897597HCID 21897597, compound

Reagents, catalysts & solvents 5

HCID 23978CopperCatalyst2×HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

For example, aryl-[(aminoalkoxy)-aryl]methanone oxime hydrochloride of structure 7 can be stirred in a suitable protic solvent such as isopropyl alcohol, methanol, ethanol or 2-methoxymethanol, any of which may be mixed with water. The mixture is treated with an appropriate base such as 45% potassium hydroxide solution or potassium carbonate with catalytic copper powder. Alternatively, the oxime of structure 7 can be stirred with an anhydrous solvent such as dimethylformamide or N-methylpyrrolidine under nitrogen. The mixture is treated with an appropriate base such as sodium hydride or potassium t-butoxide with catalytic copper powder. The reaction is held at a temperature from 40° C. to approximately 80° C., for a period of 4 hours to overnight. The mixture can be cooled and filtered, and the crude product isolated and purified by methods known to one skilled in the art, to give the appropriate substituted benzisoxazole or pyridylisoxazole of compound 1(f).

Workup

  1. waitThe reaction is held at a temperature from 40° C. to approximately 80° C., for a period of 4 hours to overnight
  2. temperatureThe mixture can be cooled
  3. filtrationfiltered
  4. customthe crude product isolated
  5. custompurified by methods

Sources & evidence

ORD record
ord-7bc2ba51b9ba41a6b1f7be42850bca00
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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