Hydrochloric Acid → HCID 22903533, compound

HRID 1440281Notes

Reaction equation

HRID 1440281 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][C:31](OC)=[O:32])[C:6]=2[CH:35]=1.CO[BH-](OC)OC.[Na+].Cl>COCCOC>[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:35]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3084262Sodium hydrido[tris(methanolato)]borate(1-)2×HCID 22903502HCID 22903502, compound

Product 1

HCID 22903533HCID 22903533, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 7-chloro-5-methoxycarbonylmethyl-1-[6-(2-chlorobenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (8 g) in ethylene glycol dimethyl ether (50 ml)is added sodium trimethoxyborohydride (6 g), and the mixture is refluxed for 4 hours. To the mixture is added sodium trimethoxyborohydride (3 g), and the mixture is refluxed for two hours. The reaction solution is gradually poured into diluted aqueous hydrochloric acid solution, 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, and recrystallized from dichloromethane-diethyl ether to give 7-chloro-5-(2-hydroxyethyl)-1-[6-(2-chlorobenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-l H-benzazepine (3.1 g) as white powder.

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. temperaturethe mixture is refluxed for two hours
  3. extractionthe mixture is extracted with dichloromethane
  4. washThe extract is washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto remove the solvent
  8. customThe residue is purified by silica gel column chromatography
  9. customrecrystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-ba0c5b82e40349a9a7138693fe2b9c38
Source dataset
uspto-grants-1996_03
Patent number
US05498609

Reaction notes

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