Hydroxyamine hydrochloride → Methyl 4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl)benzoate

HRID 1872376Notes

Reaction equation

HRID 1872376 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:17][CH:16]=2)=[O:14])=[CH:7][CH:6]=1)=[O:4].Cl.[NH2:29]O>CO.C(OCC)(=O)C>[CH2:22]([O:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[O:14][N:29]=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=3)[CH:12]=2)=[CH:16][CH:17]=1)[CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 11405985Methyl 4-[1,3-dioxo-3-[4-(pentyloxy)phenyl]propyl]benzoate

Product 1

HCID 10737571Methyl 4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl)benzoateYield 74.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The solution of 1-(4-Methoxycarbonylphenyl)-3-(4-pentyloxyphenyl)propane-1,3-dione (1.00 g) and hydroxylamine hydrochloride (567 mg) in methanol (10 ml) was refluxed for 10 hours. The reaction mixture was diluted with ethyl acetate (50 ml) and washed with water (50 ml×2), brine (50 ml). The organic layer was dried over magnesium sulfate and the solvents were removed under reduced pressure. The residue was triturated with acetonitrile (10 ml), collected by filtration, and dried under reduced pressure to give Methyl 4-[5-(4-pentyloxyphenyl)isoxazol-3-yl]benzoate (0.74 g).

Workup

  1. washwashed with water (50 ml×2), brine (50 ml)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customthe solvents were removed under reduced pressure
  4. customThe residue was triturated with acetonitrile (10 ml)
  5. filtrationcollected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-b82454a4a6e24f2490b613e6dbd95cd6
Source dataset
uspto-grants-2000_08
Patent number
US06107458

Reaction notes

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