Acetic Anhydride → N'-(3-methyl-5-nitropyridin-2-yl)acetohydrazide

HRID 873918Notes

Reaction equation

HRID 873918 reaction equation
[NH:1]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([N+:10]([O-:12])=[O:11])=[CH:5][N:4]=1)[NH2:2].[CH3:13][C:14](OC(C)=O)=[O:15]>O1CCOCC1>[CH3:9][C:8]1[C:3]([NH:1][NH:2][C:14](=[O:15])[CH3:13])=[N:4][CH:5]=[C:6]([N+:10]([O-:12])=[O:11])[CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 42361322-Hydrazinyl-3-methyl-5-nitropyridine

Product 1

HCID 84818704N'-(3-methyl-5-nitropyridin-2-yl)acetohydrazideYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension 2-hydrazinyl-3-methyl-5-nitropyridine (Step 67.1) (33.2 g, 198 mmol) in dioxane (175 mL) was added Ac2O (20.5 mL, 217 mmol) and the reaction was stirred at RT for min. The reaction mixture was poured onto ice-water and stirred for 1 hr at 0° C. The precipitate was collected by filtration, washed with H2O and Et2O, and dried under reduced pressure at 50° C. to afford the title product (41.5 g, 198 mmol, 99.5% yield) as light beige solid. tR: 0.45 min (LC-MS 2); ESI-MS: 211 [M+H]+; ESI-MS: 209 [M−H]− (LC-MS 2).

Workup

  1. additionThe reaction mixture was poured onto ice-water
  2. stirringstirred for 1 hr at 0° C
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with H2O and Et2O
  5. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-09bdcfece15d45468ded2e7d9a311ac3
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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