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Ethanol → HCID 9822781, compound

HRID 1736407
Notes
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Reaction equation

HRID 1736407 reaction equation
C(O)C.[N+:4]([C:7]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][S:22]([C:24]2[N:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])[CH:26]=[CH:27][N:28]=2)=[O:23])=[CH:14][C:8]=1[CH:9]=[CH:10][C:11](O)=[O:12])([O-])=O.[H][H]>[C].[Pd].C(N(CC)CC)C>[CH3:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[N:25]1[CH:26]=[CH:27][N:28]=[C:24]1[S:22]([CH2:21][CH2:20][CH2:19][O:18][C:15]1[CH:14]=[C:8]2[C:7](=[CH:17][CH:16]=1)[NH:4][C:11](=[O:12])[CH2:10][CH2:9]2)=[O:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 702EthanolHCID 53900945HCID 53900945, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9822781HCID 9822781, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst
HCID 8471
Triethylamine
Solvent

Procedure

To 50 ml of ethanol were added 300 mg of 2-nitro-5-{3-[1-(2-methylphenyl)-2-imidazolylsulfinyl]-propoxy}cinnamic acid, 100 mg of 10% palladium carbon and 0.6 ml of triethylamine. Hydrogenation was conducted at a hydrogen pressure of 4 atm. at 60° C. for 3 hours. The reaction mixture was cooled to room temperature and filtered to remove the catalyst. To the filtrate was added 200 mg of 10% palladium carbon, and hydrogenation was conducted at a hydrogen pressure of 4 atm. at 60° C. for 6 hours. Ethanol was removed by distillation. The residue was made acidic with hydrochloric acid, followed by extraction with methylene chloride. The extract was washed with an aqueous solution saturated with sodium chloride, dried with anhydrous magnesium sulfate, and subjected to distillation to remove the solvent. The residue was purified by a silica gel column chromatography (eluant: dichloromethane/methanol=50/1→20/1). The crude crystals were recrystallized from ethanol-n-hexane to obtain 70 mg of 6-{3-[1-(2-methylphenyl)-2-imidazolylsulfinyl]propoxy}-3,4-dihydrocarbostyril.

Workup

  1. filtrationfiltered
  2. customto remove the catalyst
  3. additionTo the filtrate was added 200 mg of 10% palladium carbon, and hydrogenation
  4. customEthanol was removed by distillation
  5. extractionfollowed by extraction with methylene chloride
  6. washThe extract was washed with an aqueous solution saturated with sodium chloride
  7. dry with materialdried with anhydrous magnesium sulfate
  8. distillationsubjected to distillation
  9. customto remove the solvent
  10. customThe residue was purified by a silica gel column chromatography (eluant: dichloromethane/methanol=50/1→20/1)
  11. customThe crude crystals were recrystallized from ethanol-n-hexane

Sources & evidence

ORD record
ord-faaaae4446624973bf409163554d0a2c
Source dataset
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05541198

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes