Hydrochloric Acid → HCID 22329089, compound

HRID 586880Notes

Reaction equation

HRID 586880 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH2:13][CH3:14])[CH2:10][CH2:9][C:8]([C:15]([O:17]C(C)(C)C)=[O:16])=[CH:7][C:6]=2[CH:22]=1.Cl.O.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][CH3:14])[CH2:10][CH2:9][C:8]([C:15]([OH:17])=[O:16])=[CH:7][C:6]=2[CH:22]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 22329011HCID 22329011, compound

Product 1

HCID 22329089HCID 22329089, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

In ethyl acetate (80 ml) was dissolved t-butyl 7-bromo-1-propyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate (8.05 g). To the solution was added a solution of 4N hydrochloric acid in ethyl acetate (80 ml), and the mixture was stirred at room temperature for 12 hours. To the mixture was added water, and the mixture was adjusted to pH2 with saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue of solid was washed with hexane-ethyl acetate to give yellow crystals of 7-bromo-1-propyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (2.61 g, 39%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. washthe residue of solid was washed with hexane-ethyl acetate

Sources & evidence

ORD record
ord-b76b5ea9dd454727b6851ec0d631d29a
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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