Tetrahydrofuran → 4-{[5-Methoxy-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentyl]amino}benzoic acid

HRID 2091243Notes

Reaction equation

HRID 2091243 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([NH:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][CH:22]=1)[C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:11]=2[C:12]=1[CH3:13].O1CCCC1.[OH-].[Na+]>C(O)C>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([NH:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)[C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:11]=2[C:12]=1[CH3:13]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66778149Methyl 4-{[5-methoxy-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentyl]amino}benzoate

Product 1

HCID 667778864-{[5-Methoxy-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentyl]amino}benzoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of methyl 4-{[5-methoxy-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentyl]amino}benzoate (1.07 g) synthesized above, tetrahydrofuran (10 mL) and ethanol (10 mL) was added 1N aqueous sodium hydroxide solution (10.0 mL), and the mixture was stirred with heating under reflux for 1 day, and concentrated under reduced pressure. The residue was dissolved in water (10 mL), and 1N hydrochloric acid (10.0 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title object compound (875 mg, 85%) as a brown solid.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 1 day
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in water (10 mL)
  5. addition1N hydrochloric acid (10.0 mL) was added at 0° C
  6. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-031f15bc033d4140acf8f683c39672b3
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

Loading…