Hydrochloric Acid → HCID 178469356, compound

HRID 340590Notes

Reaction equation

HRID 340590 reaction equation
[F:1][C:2]1[C:7]([NH:8][NH2:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:16](OCC)(=[O:24])[C:17]#[C:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].Cl>C(O)C>[F:1][C:2]1[C:7]([N:8]2[C:16]([OH:24])=[CH:17][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 69803Diethyl acetylenedicarboxylateHCID 552809452-Fluoro-3-hydrazinylpyridine

Product 1

HCID 178469356HCID 178469356, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-fluoro-3-hydrazinopyridine (30.0 g) in ethanol (472 mL) were added sodium carbonate (65.2 g) and diethyl but-2-ynedioate (40.2 g). After refluxing for 18 hr, the mixture was cooled to room temperature, treated with 2 mol/L hydrochloric acid, and extracted twice with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was suspended in diethyl ether, and the obtained solid was collected by filtration and dried under reduced pressure to give the title compound as a yellow solid (yield 20.0 g, yield 34%).

Workup

  1. temperatureAfter refluxing for 18 hr
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. filtrationthe obtained solid was collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-3303946d6dc64b3382b0c9c5a1935f23
Source dataset
uspto-grants-2014_11
Patent number
US08895588B2

Reaction notes

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