Water → HCID 22903515, compound

HRID 1440261Notes

Reaction equation

HRID 1440261 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:29])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH3:27])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH:7]([O:30][CH2:31][C:32]([O:34]C)=[O:33])[C:6]=2[CH:36]=1.[OH-].[Na+].O>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:29])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH3:27])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH:7]([O:30][CH2:31][C:32]([OH:34])=[O:33])[C:6]=2[CH:36]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 22903509HCID 22903509, compound

Product 1

HCID 22903515HCID 22903515, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 7-chloro-5-methoxycarbonylmethoxy-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.4 g) in ethanol (5 ml) is added 5N aqueous sodium hydroxide solution (1 ml), and the mixture is stirred at room temperature for 4 hours. Water is added to the reaction mixture, and the mixture is made weak acidic by adding thereto diluted hydrochloric acid, and extracted with dichloromethane. The extract is washed with water, dried over magnesium sulfate, and evaporated under reduced pressure to remove the solvent. The residue is crystallized from diethyl ether to give 7-chloro-5-carboxymethoxy-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.38 g) as white powder.

Workup

  1. additionby adding
  2. extractiondiluted hydrochloric acid, and extracted with dichloromethane
  3. washThe extract is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customto remove the solvent
  7. customThe residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-205b740b95f9498199fba3522ae9ee2d
Source dataset
uspto-grants-1996_03
Patent number
US05498609

Reaction notes

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