Hydrochloric Acid → HCID 57438650, compound

HRID 1098147Notes

Reaction equation

HRID 1098147 reaction equation
[ClH:1].O1CCOCC1.[CH3:8][C:9]1[C:14]([N:15](C(OC(C)(C)C)=O)[NH:16]C(OC(C)(C)C)=O)=[CH:13][CH:12]=[CH:11][N:10]=1>CC(O)C.C(OCC)C>[ClH:1].[NH:15]([C:14]1[C:9]([CH3:8])=[N:10][CH:11]=[CH:12][CH:13]=1)[NH2:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57438649HCID 57438649, compound

Product 1

HCID 57438650HCID 57438650, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Procedure

is Hydrogen chloride in dioxane (5.67 mL, 22.67 mmol) was added to a solution of di-tert-butyl 1-(2-methylpyridin-3-yl)hydrazine-1,2-dicarboxylate (Intermediate V1) (733 mg, 2.27 mmol) in IPA (10 mL). The reaction mixture was heated at reflux for 20 mins. The reaction mixture was allowed to cool and then diluted with diethyl ether (30 mL). The resultant precipitate was collected by filtration and dried in vacuo to afford 3-hydrazinyl-2-methylpyridine hydrochloride (362 mg, 100%). 1H NMR (400 MHz, DMSO) δ 2.66 (3H, s), 7.80-7.83 (1H, m), 7.95-7.97 (1H, m), 8.23-8.25 (1H, m), 9.15 (1H, s), 11.30 (1H, s); no ion in LCMS (1NH missing).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 20 mins
  3. temperatureto cool
  4. filtrationThe resultant precipitate was collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-5f19772db3aa47d5acd3ef17adf120d8
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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