Tetrahydrofuran → 4-{[3-Methyl-1-(3-methyl-1-benzofuran-2-yl)butyl]amino}benzoic acid

HRID 2091006Notes

Reaction equation

HRID 2091006 reaction equation
[CH3:1][CH:2]([CH3:26])[CH2:3][CH:4]([NH:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=1)[C:5]1[O:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]=1[CH3:10].O1CCCC1.[OH-].[Na+]>C(O)C>[CH3:1][CH:2]([CH3:26])[CH2:3][CH:4]([NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:24][CH:25]=1)[C:5]1[O:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[C:9]=1[CH3:10]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium Hydroxide2×HCID 66777907Methyl 4-{[3-methyl-1-(3-methyl-1-benzofuran-2-yl)butyl]amino}benzoate

Product 1

HCID 667774354-{[3-Methyl-1-(3-methyl-1-benzofuran-2-yl)butyl]amino}benzoic acidYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of methyl 4-{[3-methyl-1-(3-methyl-1-benzofuran-2-yl)butyl]amino}benzoate (1.38 g) synthesized above, tetrahydrofuran (20 mL) and ethanol (20 mL) was added 1N aqueous sodium hydroxide solution (20 mL), and the mixture was stirred with heating under reflux overnight. In addition, 1N aqueous sodium hydroxide solution (20 mL) was added, and the mixture was stirred with heating under reflux for 3 hr. The reaction mixture was concentrated under reduced pressure, 1N hydrochloric acid (40 mL) was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with diisopropyl ether to give the title object compound (1.06 g, 80%) as a white solid.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux overnight
  3. stirringthe mixture was stirred
  4. temperaturewith heating
  5. temperatureunder reflux for 3 hr
  6. concentrationThe reaction mixture was concentrated under reduced pressure, 1N hydrochloric acid (40 mL)
  7. additionwas added to the residue
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe extract was washed with water and saturated brine
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-9c6eed146ac54114bcd2f933ab9f8045
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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