Acetic Acid → ethyl (2E)-3-[2-(4-cyanopyridin-2-yl)hydrazinyl]prop-2-enoate

HRID 514380

Reaction equation

HRID 514380 reaction equation
[NH:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][N:10]=1)[C:6]#[N:7])[NH2:2].CN(C)/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16].CC(O)=O>CCO>[C:6]([C:5]1[CH:8]=[CH:9][N:10]=[C:3]([NH:1][NH:2]/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:4]=1)#[N:7]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5369162Ethyl trans-3-dimethylaminoacrylateHCID 201187142-Hydrazinylpyridine-4-carbonitrile

Product 1

HCID 86725509ethyl (2E)-3-[2-(4-cyanopyridin-2-yl)hydrazinyl]prop-2-enoateYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-hydrazinylisonicotinonitrile (500 mg, 3.73 mmol, PREPARATION 2) and ethyl (2E)-3-(dimethylamino)prop-2-enoate (534 mg, 3.73 mmol) in 20 mL EtOH was added 4 mL AcOH, before the mixture was heated under reflux conditions overnight. The reaction mixture was cooled and concentrated to dryness. The residue was adjusted to pH >8 with sat'd. aq. NaHCO3 and extracted with EtOAc. The combined organic layers were washed with brine, dried, and concentrated to dryness. The residue was purified by flash column chromatography (PE/EtOAc=5/1) to give the title compound (300 mg, 35%) as a yellow solid. [M+H] Calc'd for C11H12N4O2, 233. Found, 233.

Workup

  1. temperaturebefore the mixture was heated under reflux conditions overnight
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated to dryness
  4. extractionaq. NaHCO3 and extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. customdried
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by flash column chromatography (PE/EtOAc=5/1)

Sources & evidence

ORD record
ord-5ae4f848546b484db7b7cbcbf35a0f68
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Linked notes

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