Hydrochloric Acid → HCID 22329205, compound

HRID 587041Notes

Reaction equation

HRID 587041 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:10][CH2:9][C:8]([C:17]([O:19]C)=[O:18])=[CH:7][C:6]=2[CH:21]=1.[OH-].[Na+].Cl>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:10][CH2:9][C:8]([C:17]([OH:19])=[O:18])=[CH:7][C:6]=2[CH:21]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22329039HCID 22329039, compound

Product 1

HCID 22329205HCID 22329205, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In THF (36 ml)/methanol (36 ml) was dissolved methyl 7-bromo-1-isopentyl-2,3-dihydro-1-benzazepine-4-carboxylate (1.8 g). To the solution was added 1N sodium hydroxide solution (18 ml), and the mixture was stirred at room temperature for 24 hours. pH was adjusted to approximate 5 with 1N hydrochloric acid, and the solvent was concentrated to half under reduced pressure. The concentrated material was extracted with ethyl acetate, 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 (=6/1) to give 7-bromo-1-isopentyl-2,3-dihydro-1-benzazepine-4-carboxylic acid (1.51 g).

Workup

  1. concentrationthe solvent was concentrated to half under reduced pressure
  2. extractionThe concentrated material was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. washthe resulting residue was washed with hexane/ethyl acetate (=6/1)

Sources & evidence

ORD record
ord-c4b9d89f798c458caa03763cd104f2fe
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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