1-Butanol → (2E)-3-[6-Methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylohydrazide dihydrochloride

HRID 546798Notes

Reaction equation

HRID 546798 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[N:9]=[C:8](/[CH:10]=[CH:11]/[C:12]([NH:14][NH:15]C(OC(C)(C)C)=O)=[O:13])[CH:7]=[CH:6][C:5]=1[N:23]1[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]1.C(O)CCC.CC(OC)(C)C>CO>[ClH:1].[ClH:1].[CH3:2][O:3][C:4]1[N:9]=[C:8](/[CH:10]=[CH:11]/[C:12]([NH:14][NH2:15])=[O:13])[CH:7]=[CH:6][C:5]=1[N:23]1[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 15413tert-Butyl methyl etherHCID 57609249HCID 57609249, compound

Product 1

HCID 46854985(2E)-3-[6-Methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylohydrazide dihydrochlorideYield 78.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Conc. HCl (5.85 mL) was added to the suspension of tert-Butyl 2-{(2E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]prop-2-enoyl}hydrazinecarboxylate (1.17 g, 3.13 mmol) in methanol (5.85 mL) with an ice-bath cooling. The reaction mixture was stirred at room temperature for 30 minutes. 1-Butanol (5.85 mL) and MTBE (5.85 mL) were added to the reaction mixture, and the mixture was stirred for 20 minutes with an ice-bath cooling. The mixture was filtrated, and the residue was washed with 1-butanol-MTBE (2:8) (5.85 mL) and dried under the reduced pressure to obtain the title compound (937 mg, 78.2% yield).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 20 minutes with an ice-bath
  3. temperaturecooling
  4. filtrationThe mixture was filtrated
  5. washthe residue was washed with 1-butanol-MTBE (2:8) (5.85 mL)
  6. customdried under the reduced pressure

Sources & evidence

ORD record
ord-80b689c7e0b74a9e9f4639f59244774a
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

Loading…