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

HRID 2091228Notes

Reaction equation

HRID 2091228 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([NH:18][C:19]3[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=3)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[C:8]([CH3:29])[C:7]=2[CH:30]=1.O1CCCC1.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11]([NH:18][C:19]3[CH:28]=[CH:27][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=3)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[C:8]([CH3:29])[C:7]=2[CH:30]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66778946Methyl 4-{[1-(5-methoxy-3-methyl-1-benzofuran-2-yl)heptyl]amino}benzoate

Product 1

HCID 667788014-{[1-(5-Methoxy-3-methyl-1-benzofuran-2-yl)heptyl]amino}benzoic acidYield 90.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of methyl 4-{[1-(5-methoxy-3-methyl-1-benzofuran-2-yl)heptyl]amino}benzoate (1.17 g) synthesized above, tetrahydrofuran (20 mL) and ethanol (20 mL) was added 1N aqueous sodium hydroxide solution (20.0 mL), and the mixture was stirred overnight with heating under reflux, and concentrated under reduced pressure. The residue was dissolved is in water (20 mL), and 1N hydrochloric acid (20.0 mL) was added at 0° C. The resulting precipitate was collected by filtration to give the title object compound (1.02 g, 90%) as a pale-brown solid.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved
  5. addition1N hydrochloric acid (20.0 mL) was added at 0° C
  6. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-8288b9024e96434ca3498d97a47e4ab9
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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