5-Methyl-3-phenylisoxazole-4-carbonyl chloride → HCID 11427907, compound

HRID 1678306Notes

Reaction equation

HRID 1678306 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13](Cl)=[O:14].[OH:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=[C:19]([CH3:27])[CH:18]=1>N1C=CC=CC=1.C(OCC)(=O)C>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([O:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=[C:19]([CH3:27])[CH:18]=1)=[O:14]

Participants

5

Reactant 2

HCID 856245-Methyl-3-phenylisoxazole-4-carbonyl chlorideHCID 1784288112-Methylquinolin-4-ol

Product 1

HCID 11427907HCID 11427907, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

5-Methyl-3-phenylisoxazole-4-carbonyl chloride (100 mg) and 4-hydroxy-2-methylquinoline (250 mg) were dissolved in dichlorormethane (10 mL) and pyridine (0.2 mL). The reaction solution was heated at 70° C. overnight and then diluted with ethyl acetate (60 mL). The organic solution was washed with water (60 mL), dried, evaporated and purified by flash column chromatography (EtOAc/hexanes=1/2) to give 5-methyl-3-phenyl-4-isoxazolecarboxylic acid, 2-methyl-4-quinolinyl ester (100 mg). 1H NMR (CDCl3): δ 2.74 (s, 3H), 2.91 (s, 3H), 7.29 (s, 1H), 7.33-7.46 (m, 5H), 7.64-7.71 (m, 3H), 8.01 (td, J=0.9 and 8.4 Hz, 1H); LCMS: ret. time: 23.10 min.; purity: 100%; MS (m/e): 345.02 (MH+).

Workup

  1. washThe organic solution was washed with water (60 mL)
  2. customdried
  3. customevaporated
  4. custompurified by flash column chromatography (EtOAc/hexanes=1/2)

Sources & evidence

ORD record
ord-05680ff7b3334959bea733f75a343b75
Source dataset
uspto-grants-2011_08
Patent number
US08008501B2

Reaction notes

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