Sodium Bicarbonate → HCID 22329277, compound

HRID 587049Notes

Reaction equation

HRID 587049 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH2:13][O:14][CH2:15][CH3:16])[CH2:10][CH2:9][C:8]([C:17]([O:19]C(C)(C)C)=[O:18])=[CH:7][C:6]=2[CH:24]=1.Cl.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH2:13][O:14][CH2:15][CH3:16])[CH2:10][CH2:9][C:8]([C:17]([OH:19])=[O:18])=[CH:7][C:6]=2[CH:24]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 22329219HCID 22329219, compound

Product 1

HCID 22329277HCID 22329277, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In ethyl acetate (22 ml) was dissolved tert-butyl 7-bromo-1-(2-ethoxyethyl)-2,3-dihydro-1-benzazepine-4-carboxylate (1.1 g). To the solution was added 4N hydrochloric acid/ethyl acetate (11 ml) at room temperature, and the mixture was stirred for 24 hours. An aqueous saturated solution of sodium hydrogen carbonate was added to adjust pH to approximate 4, followed by extraction with ethyl acetate. The extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was washed with hexane/ethyl acetate (=8/1) to give 7-bromo-1-(2-ethoxyethyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (0.73 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried with magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. washthe resulting residue was washed with hexane/ethyl acetate (=8/1)

Sources & evidence

ORD record
ord-112608170eae4f6dbd2ef203da3628c6
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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