Sodium Hydroxide → 1-cyclopropylmethyl-7-[4-(2-propoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid

HRID 586933Notes

Reaction equation

HRID 586933 reaction equation
[CH:1]1([CH2:4][N:5]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][CH3:28])=[CH:18][CH:17]=4)=[CH:15][C:10]=3[CH:9]=[C:8]([C:29]([O:31]C)=[O:30])[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[OH-].[Na+]>CO.C1COCC1>[CH:1]1([CH2:4][N:5]2[C:11]3[CH:12]=[CH:13][C:14]([C:16]4[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][CH3:28])=[CH:20][CH:21]=4)=[CH:15][C:10]=3[CH:9]=[C:8]([C:29]([OH:31])=[O:30])[CH2:7][CH2:6]2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22329229HCID 22329229, compound

Product 1

HCID 223290701-cyclopropylmethyl-7-[4-(2-propoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylic acidYield 91.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In methanol (25 ml) and THF (25 ml) was dissolved methyl 1-cyclopropylmethyl-7-[4-(2-propoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.34 g). To the solution was added 1N sodium hydroxide solution (7.5 ml), and the mixture was stirred at room temperature overnight, heated at 50° C. for 1 hour, concentrated, which was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate. The solvent was evaporated to give 1-cyclopropylmethyl-7-[4-(2-propoxyethoxy)phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.30 g) as yellow crystals.

Workup

  1. temperatureheated at 50° C. for 1 hour
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-4e41165d6462419aa8dbb38ae6778b60
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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