Hydroxyamine hydrochloride → HCID 22621197, compound

HRID 1953112Notes

Reaction equation

HRID 1953112 reaction equation
Cl.NO.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:22])[C:12](=[CH:18][N:19](C)C)[C:13]([CH:15]2[CH2:17][CH2:16]2)=[O:14])=[C:7]([N:23]([CH3:27])[C:24](=[O:26])[CH3:25])[CH:6]=1>C(O)C>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:12]2[CH:18]=[N:19][O:14][C:13]=2[CH:15]2[CH2:17][CH2:16]2)=[O:22])=[C:7]([N:23]([CH3:27])[C:24](=[O:26])[CH3:25])[CH:6]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 54444496HCID 54444496, compound

Product 1

HCID 22621197HCID 22621197, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (0.1 g) was added to a stirred solution of 1-[4-chloro-2-(N-methylacetamido)phenyl]-3-cyclopropyl-2-dimethylaminomethylenepropane-1,3-dione (0.32 g) in ethanol. The mixture was stirred for 0.75 hours and evaporated to dryness. Water was added to the residue, which was extracted (dichloromethane). The extract was dried (magnesium sulphate) and evaporated to give an oil. This was purified by chromatography eluting with ethyl acetate/dichloromethane (1:8) to give 4-[4-chloro-2-(N-methylacetamido)benzoyl]-5-cyclopropylisoxazole, (compound number 1, 0.12 g), m.p. 106.5-107.5° C., as a white solid.

Workup

  1. customevaporated to dryness
  2. additionWater was added to the residue, which
  3. extractionwas extracted (dichloromethane)
  4. dry with materialThe extract was dried (magnesium sulphate)
  5. customevaporated
  6. customto give an oil
  7. customThis was purified by chromatography
  8. washeluting with ethyl acetate/dichloromethane (1:8)

Sources & evidence

ORD record
ord-444df441b61b439dbadd245bce7c5e33
Source dataset
uspto-grants-2000_09
Patent number
US06114538

Reaction notes

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