Hydrazine → 2-Hydrazinyl-4-(2-methoxyethoxy)pyridine

HRID 339661Notes

Reaction equation

HRID 339661 reaction equation
[NH2:1][NH2:2].Cl[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])[CH:7]=[CH:6][N:5]=1>N1C=CC=CC=1>[NH:1]([C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])[CH:7]=[CH:6][N:5]=1)[NH2:2]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 637775772-Chloro-4-(2-methoxyethoxy)pyridine

Product 1

HCID 552790432-Hydrazinyl-4-(2-methoxyethoxy)pyridineYield 33%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Hydrazine (10 mL, 318.6 mmol) was added to a solution of 2-chloro-4-(2-methoxyethoxy)pyridine (1.00 g, 5.330 mmol) in pyridine (25 mL). The reaction was heated to reflux. After 18 hours the reaction mixture was partitioned between H2O and DCM and the aqueous phase was extracted with DCM. The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified via flash column chromatography (40:1 DCM/MeOH followed by 20:1 DCM/MeOH) to provide 320 mg (33%) of desired product as a white solid.

Workup

  1. temperatureThe reaction was heated to reflux
  2. customAfter 18 hours the reaction mixture was partitioned between H2O and DCM
  3. extractionthe aqueous phase was extracted with DCM
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified via flash column chromatography (40:1 DCM/MeOH followed by 20:1 DCM/MeOH)

Sources & evidence

ORD record
ord-e5364d81bc16429eaeb6dee09052c3e8
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Reaction notes

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