Hydrazine hydrate (1:1) → 2-Hydrazinyl-5-methoxypyridine

HRID 1437258Notes

Reaction equation

HRID 1437258 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][N:3]=1.O.[NH2:11][NH2:12]>>[NH:11]([C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][N:3]=1)[NH2:12]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 151690002-Chloro-5-methoxypyridine

Product 1

HCID 230902452-Hydrazinyl-5-methoxypyridine

Procedure

The above-obtained 2-chloro-5-methoxypyridine (4.0 g) in hydrazine monohydrate (30 mL) was stirred at 100° C. for 24 hours, and then cooled in air. The reaction solvent was removed under reduced pressure, and the residue was partitioned by use of chloroform and aqueous 1N sodium hydroxide. The organic layer was dried over magnesium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, to thereby give 2-hydrazino-5-methoxypyridine as an oily product (705 mg, 18%).

Workup

  1. temperaturecooled in air
  2. customThe reaction solvent was removed under reduced pressure
  3. customthe residue was partitioned by use of chloroform and aqueous 1N sodium hydroxide
  4. dry with materialThe organic layer was dried over magnesium sulfate anhydrate
  5. filtrationfollowed by filtration
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5ef3b5688d254272ae3d74ff557b17fd
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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