Sodium Hydroxide → 7-[4-[N-ethyl-N-(2-propoxyethyl)amino]phenyl]-1-formyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid

HRID 586860Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

In methanol (25 ml) and THF (25 ml) was dissolved methyl 7-[4-[N-ethyl-N-(2-propoxyethyl)amino]phenyl]-1-formyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.31 g). To the solution was added 1N sodium hydroxide solution (7 ml), and the mixture was stirred at 60° C. for 1.5 hours and concentrated. To the residue was added water, and the mixture was 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, and the solvent was evaporated to give 7-[4-[N-ethyl-N-(2-propoxyethyl)amino]phenyl]-1-formyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.29 g) as pale yellow crystals.

Workup

concentrationconcentrated
additionTo the residue was added water
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-9e1576cb30dc4c97bd752bf8a85ed491
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06936602B1

Reaction notes

Loading…