Hydrochloric Acid → HCID 22903517, compound

HRID 1489083Notes

Reaction equation

HRID 1489083 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:32])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:31])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]([O:29]C)=[O:28])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH:7]([OH:33])[C:6]=2[CH:34]=1.[OH-].[Na+].O.Cl>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:32])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:31])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]([OH:29])=[O:28])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH:7]([OH:33])[C:6]=2[CH:34]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 22903500HCID 22903500, compound

Product 1

HCID 22903517HCID 22903517, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 7-chloro-5-hydroxy-1-[6-(2-methoxycarbonylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.3 g) in methanol (4 ml) is added 5% aqueous sodium hydroxide solution (1.5 ml), and the mixture is stirred at room temperature for one hour. To the reaction solution are added water and diluted aqueous hydrochloric acid solution in order to make the mixture weak acidic. The mixture is extracted with dichloromethane, and the extract is washed with water, dried over magnesium sulfate and evaporated under reduced pressure to remove the solvent. The residue is recrystallized from dichloromethane-methanol to give 7-chloro-5-hydroxy-1-[6-(2-carboxybenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (150 mg) as white powder.

Workup

  1. extractionThe mixture is extracted with dichloromethane
  2. washthe extract is washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customto remove the solvent
  6. customThe residue is recrystallized from dichloromethane-methanol

Sources & evidence

ORD record
ord-76ec6f4832474a57be5fa7c55c47492f
Source dataset
uspto-grants-1997_10
Patent number
US05677299

Reaction notes

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