Sodium Hydroxide → 6-(6,7-Dimethoxyquinolin-4-yloxy)benzofuran-3-carboxylic acid

HRID 1865216Notes

Reaction equation

HRID 1865216 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:28]=[CH:27][C:19]2[C:20]([C:23]([O:25]C)=[O:24])=[CH:21][O:22][C:18]=2[CH:17]=1.[OH-].[Na+]>O1CCOCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:28]=[CH:27][C:19]2[C:20]([C:23]([OH:25])=[O:24])=[CH:21][O:22][C:18]=2[CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69019235Methyl 6-(6,7-dimethoxyquinolin-4-yloxy)benzofuran-3-carboxylate

Product 1

HCID 690186826-(6,7-Dimethoxyquinolin-4-yloxy)benzofuran-3-carboxylic acidYield 66.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 6-(6,7-dimethoxyquinolin-4-yloxy)benzofuran-3-carboxylate (102 mg, 0.269 mmol) was dissolved in dioxane (1.6 mL) and water (0.5 mL), then added 2N aqueous sodium hydroxide (141 □L). The reaction mixture was stirred at room temperature overnight. The mixture was concentrated in vacuo then diluted with water. The aqueous layer was extracted with ethyl acetate. The aqueous layer was acidified with aqueous 1N hydrochloric acid (282 μL) and the precipitate was collected, washed with water and dried under high vacuum to give 6-(6,7-dimethoxyquinolin-4-yloxy)benzofuran-3-carboxylic acid as a light yellow solid (65 mg). MS (ESI, pos. ion) m/z: 366.1 (M+1).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthen diluted with water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. customthe precipitate was collected
  5. washwashed with water
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-03078efab9794cfbb2e7ede200e19631
Source dataset
uspto-grants-2009_12
Patent number
US07626030B2

Reaction notes

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