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

HRID 586993Notes

Reaction equation

HRID 586993 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[CH2:10][CH2:9][C:8]([C:18]([O:20]C)=[O:19])=[CH:7][C:6]=2[CH:22]=1.[OH-].[Na+].O.Cl>O1CCCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[CH2:10][CH2:9][C:8]([C:18]([OH:20])=[O:19])=[CH:7][C:6]=2[CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22329130Methyl 7-bromo-1-(2-thienylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate

Product 1

HCID 223290607-Bromo-1-(2-thienylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylic acidYield 73.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 7-bromo-1-(2-thienylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylate (810 mg) in a mixture of tetrahydrofuran (60 ml) and methanol (60 ml) was added 1N sodium hydroxide solution (21 ml), and the mixture was stirred at room temperature overnight. Then, to the mixture was added water at 0° C., and 1N hydrochloric acid was further added to make acidic (pH=4), 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, and the resulting solid was recrystallized from hexane-ethyl acetate to give 7-bromo-1-(2-thienylmethyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (574 mg) as yellow 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 magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe resulting solid was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-f949e799129c480bb70f2a9201978606
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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