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Water → HCID 22903506, compound

HRID 1440282
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Reaction equation

HRID 1440282 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[Cl:27])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH:7]([CH2:30][CH2:31][OH:32])[C:6]=2[CH:33]=1.[C:34](OC(=O)C)(=[O:36])[CH3:35].O>N1C=CC=CC=1>[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[Cl:27])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH:7]([CH2:30][CH2:31][O:32][C:34](=[O:36])[CH3:35])[C:6]=2[CH:33]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 22903533HCID 22903533, compound

Product 1

HCID 22903506HCID 22903506, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 7-chloro-5-(2-hydroxyethyl)-1-[6-(2-chlorobenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.3 g) in pyridine (6 ml) is added acetic anhydride (0.09 ml), and the mixture is stirred at 80° C. for 2 hours. The reaction solution is poured into water, and extracted with ethyl acetate. The extract is washed successively with diluted hydrochloric acid, water and aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate, and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography, and recrystallized from dichloromethane-diethyl ether to give 7-chloro-5-(2-acetyloxyethyl)-1-[6-(2-chlorobenzoylamino )nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (230 mg) as white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is washed successively with diluted hydrochloric acid, water and aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customto remove the solvent
  6. customThe residue is purified by silica gel column chromatography
  7. customrecrystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-906b458ac9944e98a5e12a28ce522f32
Source dataset
uspto-grants-1996_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05498609

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes