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

HRID 1440257Notes

Reaction equation

HRID 1440257 reaction equation
[CH3:1]C(C)([O-])C.[K+].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[N:17]([C:18](=[O:35])[C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:34])[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[CH3:33])=[N:21][CH:20]=3)[CH2:16][CH2:15][CH2:14][C:13](=O)[C:12]=2[CH:37]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[N:17]([C:18](=[O:35])[C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:34])[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[CH3:33])=[N:21][CH:20]=3)[CH2:16][CH2:15][CH2:14][C:13](=[CH2:1])[C:12]=2[CH:37]=1

Participants

5

Reactant 2

HCID 229035137-chloro-5-oxo-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepineHCID 23665647Potassium tert-butoxide

Product 1

HCID 229034667-chloro-5-methylidene-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepineYield 48.5%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

To a suspension of methyltriphenylphosphonium bromide (0.86 g) in tetrahydrofuran (20 ml) is added with stirring potassium t-butoxide (0.23 g) at -5° C., and the mixture is stirred at -5° C. for one hour. To the mixture is added 7-chloro-5-oxo-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.58 g) at the same temperature, and the mixture is stirred at room temperature for one hour. The reaction mixture is poured into ice-water, and extracted with ethyl acetate. The extract is washed with water, dried over magnesium sulfate, and evaporated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography to give 7-chloro-5-methylidene-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.28 g) as yellow amorphous.

Workup

  1. stirringthe mixture is stirred at room temperature for one hour
  2. extractionextracted with ethyl acetate
  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 purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8f827ca091f3470c94df22f5b3437df2
Source dataset
uspto-grants-1996_03
Patent number
US05498609

Reaction notes

Loading…