Sodium Bicarbonate → Ethyl 7-bromo-2,3-dihydro-1-benzazepine-4-carboxylate

HRID 1388075Notes

Reaction equation

HRID 1388075 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11](C=O)[CH2:10][CH2:9][C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7][C:6]=2[CH:19]=1.C(=O)([O-])O.[Na+]>Cl.C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][CH2:10][CH2:9][C:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7][C:6]=2[CH:19]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 18472216Ethyl 7-bromo-1-formyl-2,3-dihydro-1-benzazepine-4-carboxylate

Product 1

HCID 18472278Ethyl 7-bromo-2,3-dihydro-1-benzazepine-4-carboxylateYield 59%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

In 1N hydrochloric acid (25 ml) and ethanol (20 ml) was dissolved ethyl 7-bromo-1-formyl-2,3-dihydro-1-benzazepine-4-carboxylate (1165 mg), and the mixture was refluxed for 2 hours. The mixture was neutralized with saturated sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate (300 ml). The organic layer was washed with water (100 ml) and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified with silica gel column chromatography (150 g, hexane/ethyl acetate=9:1) to give ethyl 7-bromo-2,3-dihydro-1-benzazepine-4-carboxylate (628 mg, 59%).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. extractionthe mixture was extracted with ethyl acetate (300 ml)
  3. washThe organic layer was washed with water (100 ml)
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified with silica gel column chromatography (150 g, hexane/ethyl acetate=9:1)

Sources & evidence

ORD record
ord-2bcbadb57d8446d09da79ec92a362ccf
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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