Hydrochloric Acid → 7-Bromo-1-formyl-2,3-dihydro-1-benzazepine-4-carboxylic acid

HRID 566144Notes

Reaction equation

HRID 566144 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.Cl>[OH-].[Na+].C1COCC1.C(O)C>[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 2

HCID 313Hydrochloric AcidHCID 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 2

HCID 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 1N 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-43915a424f4345c4b4584769d254a322
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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