Sodium Hydroxide → HCID 22329327, compound

HRID 586942Notes

Reaction equation

HRID 586942 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([C:25]4[CH:30]=[CH:29][C:28]5[O:31][CH2:32][O:33][C:27]=5[CH:26]=4)[CH2:23][CH2:22][C:21]([C:34]([O:36]C)=[O:35])=[CH:20][C:19]=3[CH:38]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>CO.C1COCC1>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:24]([C:25]4[CH:30]=[CH:29][C:28]5[O:31][CH2:32][O:33][C:27]=5[CH:26]=4)[CH2:23][CH2:22][C:21]([C:34]([OH:36])=[O:35])=[CH:20][C:19]=3[CH:38]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22329151HCID 22329151, compound

Product 1

HCID 22329327HCID 22329327, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In methanol (25 ml) and THF (25 ml) was dissolved methyl 7-[4-(2-butoxyethoxy)phenyl]-1-(3,4-methylenedioxyphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.3 g). To the solution was added 1N sodium hydroxide solution (6 ml), and the mixture was refluxed for 2 hours, concentrated, neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate. The solvent was evaporated to give 7-[4-(2-butoxyethoxy)phenyl]-1-(3,4-methylenedioxyphenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.26 g) as yellow crystals.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-eb79f805d46a4757bcda31bce00b7233
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

Loading…