Hydrochloric Acid → Methyl 7-bromo-2,3-dihydro-1H-1-benzazepine-4-carboxylate

HRID 586833Notes

Reaction equation

HRID 586833 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9][C:8]([C:19]([O:21][CH3:22])=[O:20])=[CH:7][C:6]=2[CH:23]=1.Cl.[OH-].[Na+]>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][C:8]([C:19]([O:21][CH3:22])=[O:20])=[CH:7][C:6]=2[CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22329270HCID 22329270, compound

Product 1

HCID 22328963Methyl 7-bromo-2,3-dihydro-1H-1-benzazepine-4-carboxylateYield 90.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

In ethyl acetate (50 ml) was dissolved methyl 7-bromo-1-(t-butoxycarbonyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (1.5 g). To the solution was added 6N hydrochloric acid (2 ml), and the mixture was heated to stir at 80° C. for 2 hours, neutralized with 1N sodium hydroxide solution 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 methyl 7-bromo-2,3-dihydro-1H-1-benzazepine-4-carboxylate (1.0 g) as yellow crystals.

Workup

  1. temperaturethe mixture was heated
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-9d37eefaa9f248b6b2a0bcd0c35b94d2
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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