Ethyl 7-bromo-1-formyl-2,3-dihydro-1-benzazepine-4-carboxylate → 7-Bromo-1-formyl-2,3-dihydro-1-benzazepine-4-carboxylic acid

HRID 2228329Notes

Reaction equation

HRID 2228329 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH:12]=[O:13])[CH2:10][CH2:9][C:8]([C:14]([O:16]CC)=[O:15])=[CH:7][C:6]=2[CH:19]=1>[OH-].[Na+].C1COCC1.C(O)C.Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH:12]=[O:13])[CH2:10][CH2:9][C:8]([C:14]([OH:16])=[O:15])=[CH:7][C:6]=2[CH:19]=1

Participants

5

Reactant 1

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

Product 1

HCID 184725177-Bromo-1-formyl-2,3-dihydro-1-benzazepine-4-carboxylic acidYield 100%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 14798Sodium HydroxideSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

In 1N sodium hydroxide (13.0 ml) and THF:ethanol (1:1, 50 ml) was dissolved ethyl 7-bromo-1-formyl-2,3-dihydro-1-benzazepine-4-carboxylate (2.77 g), and the mixture was stirred at room temperature for 15 hours. To the mixture was added IN hydrochloric acid (12.5 ml), and the mixture was concentrated. To the residue was added water (200 ml), and the mixture was adjusted to pH 2 with 1N hydrochloric acid. The mixture was extracted with ethyl acetate (300 ml×3), and the organic layer was dried with magnesium sulfate. The solvent was evaporated under reduced pressure to give 7-bromo-1-formyl-2,3-dihydro-1-benzazepine-4-carboxylic acid (2.52 g, 100%).

Workup

  1. concentrationthe mixture was concentrated
  2. additionTo the residue was added water (200 ml)
  3. extractionThe mixture was extracted with ethyl acetate (300 ml×3)
  4. dry with materialthe organic layer was dried with magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-007e626188214813bb002febfe8e3aa0
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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