3-Butenoic acid → {3-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acetic acid

HRID 1245383Notes

Reaction equation

HRID 1245383 reaction equation
[CH:1]([CH2:3][C:4]([OH:6])=[O:5])=[CH2:2].[CH3:7][C:8]1[CH:17]=[C:16]([CH2:18][O:19][C:20]2[CH:28]=[CH:27][C:23]([CH:24]=[N:25][OH:26])=[CH:22][CH:21]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1>C1COCC1>[CH3:7][C:8]1[CH:17]=[C:16]([CH2:18][O:19][C:20]2[CH:21]=[CH:22][C:23]([C:24]3[CH2:2][CH:1]([CH2:3][C:4]([OH:6])=[O:5])[O:26][N:25]=3)=[CH:27][CH:28]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1

Participants

4

Reactant 2

HCID 327433-Butenoic acidHCID 738530794-(2-Methyl-quinolin-4-ylmethoxy)-benzaldehyde oxime

Product 1

HCID 21911127{3-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acetic acidYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Clorox® was added dropwise (1 mL) to a solution of vinyl acetic acid (0.071 g, 0.8 mmol) and 4-(2-methyl-quinolin-4-ylmethoxy)-benzaldehyde oxime (0.12 g, 0.40 mmol) in THF (4 mL) under nitrogen atmosphere at room temperature. The reaction was stirred overnight, partitioned between ethyl acetate and water saturated KH2PO4 solution. The organic layer was washed with brine, dried over magnesium sulfate and concentrated to give {3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-acetic acid (0.15 g, 100%) as a crude solid. MS found: (M+H)+=377.

Workup

  1. custompartitioned between ethyl acetate and water saturated KH2PO4 solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9b397f934b354205b58aa3c8b6232569
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Reaction notes

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