Sodium Hydroxide → 1-butyl-7-[4-(2-propoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid

HRID 586919Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

In methanol (25 ml) and THF (25 ml) was dissolved methyl 1-butyl-7-[4-(2-propoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.5 g). To the solution was added 1N sodium hydroxide solution (17 ml), and the mixture was heated to stir at 50° C. for 5 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 1-butyl-7-[4-(2-propoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.38 g) as yellow crystals.

Workup

temperaturethe mixture was heated
concentrationconcentrated
extractionextracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialdried with anhydrous magnesium sulfate
customThe solvent was evaporated

Sources & evidence

ORD record: ord-1c24ff45fd9a40e99b5a6413d39a3f28
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06936602B1

Reaction notes

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