Water → 7-chloro-5-oxo-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine

HRID 1440255Notes

Reaction equation

HRID 1440255 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:20])[C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][C:7](=[O:21])[C:6]=2[CH:22]=1.[CH3:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27].O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:20])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:26](=[O:27])[C:25]4[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=4[CH3:23])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][C:7](=[O:21])[C:6]=2[CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 702762-Methylbenzoyl chlorideHCID 22903494HCID 22903494, compound

Product 1

HCID 229035137-chloro-5-oxo-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepineYield 87.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 7-chloro-5-oxo-1-(6-aminonicotinoyl)-2,3,4,5-tetrahydro-1H-benzazepine (0.25 g) in pyridine (2 ml) is added with stirring 2-methylbenzoyl chloride (0.18 g) under ice-cooling, and the mixture is stirred at room temperature for one hour. To the reaction solution is added water, and the mixture is extracted with ethyl acetate. The extract is washed successively with 0.1N aqueous hydrochloric acid solution and water, and dried over magnesium sulfate. The resultant is evaporated under reduced pressure to remove the solvent, and the residue is purified by silica gel column chromatography to give 7-chloro-5-oxo-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.3 g) as colorless amorphous.

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe extract is washed successively with 0.1N aqueous hydrochloric acid solution and water
  4. dry with materialdried over magnesium sulfate
  5. customThe resultant is evaporated under reduced pressure
  6. customto remove the solvent
  7. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ddf05de44bbc461e960dbf225ec1a21d
Source dataset
uspto-grants-1996_03
Patent number
US05498609

Reaction notes

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