Hydrochloric Acid → 1-Allyl-7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid

HRID 586981Notes

Reaction equation

HRID 586981 reaction equation
[CH2:1]([N:4]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH3:27])=[CH:17][CH:16]=3)=[CH:14][C:9]=2[CH:8]=[C:7]([C:28]([O:30]C)=[O:29])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[OH-].[Na+].O.Cl>O1CCCC1.CO>[CH2:1]([N:4]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]3[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][CH3:27])=[CH:19][CH:20]=3)=[CH:14][C:9]=2[CH:8]=[C:7]([C:28]([OH:30])=[O:29])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 69747248Methyl 1-allyl-7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylate

Product 1

HCID 697493651-Allyl-7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylic acidYield 78.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1-allyl-7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylate (262 mg) in a mixture of tetrahydrofuran (19 ml) and methanol (19 ml) was added 1N sodium hydroxide solution (6.3 ml), and the mixture was stirred at room temperature overnight. Then, water and 1N hydrochloric acid were added to make acidic (pH=4) at 0° C., and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with magnesium sulfate. The solvent was evaporated under reduced pressure to give the solid, which was washed with hexane to give 1-allyl-7-(4-propoxyethoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (199 mg) as yellow crystals.

Workup

  1. customat 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customto give the solid, which
  7. washwas washed with hexane

Sources & evidence

ORD record
ord-e24e4003745447709311af69bede31a5
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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