Sodium Hydroxide → HCID 19607905, compound

HRID 745078Notes

Reaction equation

HRID 745078 reaction equation
C([O:3][C:4]([CH2:6][O:7][CH:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([C:19](=[O:37])[C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:36])[C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=3[Cl:35])=[CH:22][CH:21]=2)[CH2:11][CH2:10][CH2:9]1)=[O:5])C.[OH-].[Na+]>C(O)C>[C:4]([CH2:6][O:7][CH:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([C:19](=[O:37])[C:20]2[CH:21]=[CH:22][C:23]([NH:26][C:27](=[O:36])[C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=3[Cl:35])=[CH:24][CH:25]=2)[CH2:11][CH2:10][CH2:9]1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19608100HCID 19608100, compound

Product 1

HCID 19607905HCID 19607905, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Ethoxycarbonylmethoxy-1-[4-(2,4-dichlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.94 g) is dissolved in ethanol (100 ml) and thereto is added 5N aqueous sodium hydroxide solution (0.50 ml). The mixture is stirred at room temperature for 2 hours. The reaction solution is concentrated under reduced pressure and to the resulting residue is added diluted hydrochloric acid and then extracted with dichloromethane. The extract is dried over magnesium sulfate and the solvent is distilled off. The resulting residue is washed with n-hexane and collected by filtration to give 5-carboxymethoxy-1-[4-(2,4-dichlorobenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.79 g) as colorless amorphous.

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure and to the resulting residue
  2. additionis added diluted hydrochloric acid
  3. extractionextracted with dichloromethane
  4. dry with materialThe extract is dried over magnesium sulfate
  5. distillationthe solvent is distilled off
  6. washThe resulting residue is washed with n-hexane
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-2bfac9e1fdb44b36944345acde18d9f6
Source dataset
uspto-grants-1996_09
Patent number
US05559230

Reaction notes

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