Hydrochloric Acid → 1-formyl-7-[4-(2-propoxy)ethoxyphenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid

HRID 586877Notes

Reaction equation

HRID 586877 reaction equation
[CH:1]([N:3]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][O:23][CH:24]([CH3:26])[CH3:25])=[CH:16][CH:15]=3)=[CH:13][C:8]=2[CH:7]=[C:6]([C:27]([O:29]C)=[O:28])[CH2:5][CH2:4]1)=[O:2].[OH-].[Na+].Cl>C1COCC1.C(O)C>[CH:1]([N:3]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][O:23][CH:24]([CH3:25])[CH3:26])=[CH:16][CH:15]=3)=[CH:13][C:8]=2[CH:7]=[C:6]([C:27]([OH:29])=[O:28])[CH2:5][CH2:4]1)=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22329024methyl 1-formyl-7-[4-(2-propoxy)ethoxyphenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Product 1

HCID 223293211-formyl-7-[4-(2-propoxy)ethoxyphenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylic acidYield 100.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixture of THF and ethanol (1:1, v/v, 30.0 ml) was dissolved methyl 1-formyl-7-[4-(2-propoxy)ethoxyphenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate (445 mg). To the solution was added 1N sodium hydroxide solution (11.0 ml), and the mixture was stirred at room temperature for 13 hours. The mixture was a little concentrated, and to the residue was added 1N hydrochloric acid to convert weakly acidic solution. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give crystals, which were washed with ethyl acetate/hexane to give 1-formyl-7-[4-(2-propoxy)ethoxyphenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (430 mg) as white crystals.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with water and saturated brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customto give crystals, which
  6. washwere washed with ethyl acetate/hexane

Sources & evidence

ORD record
ord-f98cbbe4e86b4be2a210fa393f4ecac2
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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