Hydrochloric Acid → 6-Methoxypyridine-2-carbohydrazide

HRID 1889034Notes

Reaction equation

HRID 1889034 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([NH:11][NH:12]C(OC(C)(C)C)=O)=[O:10])[CH:6]=[CH:5][CH:4]=1.Cl>O1CCOCC1>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([NH:11][NH2:12])=[O:10])[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 665988541,1-Dimethylethyl 2-{[6-(methyloxy)-2-pyridinyl]carbonyl}hydrazinecarboxylate

Product 1

HCID 242291726-Methoxypyridine-2-carbohydrazideYield 167.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1,1-dimethylethyl 2-{[6-(methyloxy)-2-pyridinyl]carbonyl}hydrazinecarboxylate (194)(1.685 g, 6.30 mmol) was dissolved in 1,4-dioxane (21.01 ml) and HCl (4M in 1,4-dioxane) (15.76 ml, 63.0 mmol) was added. The solution was stirred at room temperature for 5 hours. LCMS showed that no starting material remained and the product had formed. The solvent was removed under reduced pressure to afford 1.76 g of the crude material. The crude material was loaded onto two 10 g SCX columns and these were washed with methanol. The product was eluted off using 2M ammonia in methanol and the solvent was removed under reduced pressure to afford the purified desired product in 0.954 g.

Workup

  1. customthe product had formed
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fca7ee8762b7489288c9e161dcee6b74
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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