Hydrochloric Acid → 2-Ethyl-6-methyl-isonicotinic acid hydrazide

HRID 1924827Notes

Reaction equation

HRID 1924827 reaction equation
C(OC([NH:8][NH:9][C:10]([C:12]1[CH:17]=[C:16]([CH3:18])[N:15]=[C:14]([CH2:19][CH3:20])[CH:13]=1)=[O:11])=O)(C)(C)C.Cl>O1CCOCC1>[CH2:19]([C:14]1[CH:13]=[C:12]([CH:17]=[C:16]([CH3:18])[N:15]=1)[C:10]([NH:9][NH2:8])=[O:11])[CH3:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67520248N'-(2-ethyl-6-methyl-pyridine-4-carbonyl)-hydrazinecarboxylic acid tert-butyl ester

Product 1

HCID 670269272-Ethyl-6-methyl-isonicotinic acid hydrazide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of crude N′-(2-ethyl-6-methyl-pyridine-4-carbonyl)-hydrazinecarboxylic acid tert-butyl ester in dioxane (10 mL) is treated with 4M HCl in dioxane (4 mL) for 6 h. The mixture is evaporated, the residue taken up in MeOH and the 2-ethyl-6-methyl-isonicotinic acid hydrazide hydrochloride is precipitated from Et2O as white foam; 1H NMR (CD3OD): δ 8.16 (s, 1H), 8.14 (s, 1H), 3.15 (q, J=7.6 Hz, 2H), 2.87 (s, 3H), 1.46 (t, J=7.6 Hz, 3H).

Workup

  1. customThe mixture is evaporated
  2. customthe 2-ethyl-6-methyl-isonicotinic acid hydrazide hydrochloride is precipitated from Et2O as white foam

Sources & evidence

ORD record
ord-7d61145a0cca4f5d8d3b54664639e34e
Source dataset
uspto-grants-2012_05
Patent number
US08178562B2

Reaction notes

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