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

HRID 2035566Notes

Reaction equation

HRID 2035566 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), then 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 by 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. temperatureheated 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 by flash column chromatography (40:1 DCM/MeOH followed by 20:1 DCM/MeOH)

Sources & evidence

ORD record
ord-9877141b52b54b3ab9675b6dd59e49f5
Source dataset
uspto-grants-2013_11
Patent number
US08575145B2

Reaction notes

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