Hydrochloric Acid → HCID 22903477, compound

HRID 1440266Notes

Reaction equation

HRID 1440266 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][CH2:32][N:33]3C(=O)C4=CC=CC=C4C3=O)[C:6]=2[CH:44]=1.O.NN.O.Cl>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][CH2:32][NH2:33])[C:6]=2[CH:44]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 22903507HCID 22903507, compound

Product 1

HCID 22903477HCID 22903477, compoundYield 127.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7-chloro-5-(2-phthalimidoethoxy)-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.26 g) in ethanol (10 ml) is added hydrazine hydrate (0.04 ml), and the mixture is refluxed for 2 hours, and cooled. Water is added to the reaction solution, and the mixture is made acidic with diluted hydrochloric acid, and washed with diethyl ether. Aqueous sodium hydroxide solution is added to the aqueous layer in order to make it basic, and the mixture is 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 purified by silica gel column chromatography to give 7-chloro-5-(2-aminoethoxy)-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.26 g) as colorless amorphous.

Workup

  1. temperaturethe mixture is refluxed for 2 hours
  2. temperaturecooled
  3. washwashed with diethyl ether
  4. additionAqueous sodium hydroxide solution is added to the aqueous layer in order
  5. extractionthe mixture is extracted with dichloromethane
  6. washThe extract is washed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated under reduced pressure
  9. customto remove the solvent
  10. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4a9a661ca4de4f719caae2d9b9a90e55
Source dataset
uspto-grants-1996_03
Patent number
US05498609

Reaction notes

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