Sodium Hydroxide → 1-formyl-7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid

HRID 586836Notes

Reaction equation

HRID 586836 reaction equation
[CH:1]([N:3]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)=[CH:16][CH:15]=3)=[CH:13][C:8]=2[CH:7]=[C:6]([C:26]([O:28]C)=[O:27])[CH2:5][CH2:4]1)=[O:2].[OH-].[Na+]>CO.C1COCC1>[CH:1]([N:3]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]3[CH:15]=[CH:16][C:17]([N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)=[CH:18][CH:19]=3)=[CH:13][C:8]=2[CH:7]=[C:6]([C:26]([OH:28])=[O:27])[CH2:5][CH2:4]1)=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22328968methyl 1-formyl-7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate

Product 1

HCID 223289221-formyl-7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylic acidYield 96.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In methanol (250 ml) and THF (250 ml) was dissolved methyl 1-formyl-7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (3.54 g). To the solution was added 1N sodium hydroxide solution (90 ml), and the mixture was stirred at room temperature overnight and concentrated. To the mixture was added water, and the mixture was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated to give 1-formyl-7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (3.30 g) as colorless crystals.

Workup

  1. concentrationconcentrated
  2. additionTo the mixture was added water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a1b2cb2ad4c44f479a152032f11eac26
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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