Acetic Anhydride → HCID 117702704, compound

HRID 873938Notes

Reaction equation

HRID 873938 reaction equation
[NH:1]([C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([N+:11]([O-:13])=[O:12])=[CH:5][N:4]=1)[NH2:2].[CH3:14][C:15](OC(C)=O)=[O:16]>O1CCOCC1>[CH3:10][O:9][C:8]1[C:3]([NH:1][NH:2][C:15](=[O:16])[CH3:14])=[N:4][CH:5]=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 22372393HCID 22372393, compound

Product 1

HCID 117702704HCID 117702704, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 2-hydrazinyl-3-methoxy-5-nitropyridine (Step 84.1) (20 g, 106 mmol) in dioxane (170 mL) was added at RT Ac2O (13.1 mL, 138 mmol) and the reaction mixture was stirred for 1 hr at RT. The reaction mixture was poured onto ice-water (700 mL) 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 (23.3 g, 101 mmol, 95% yield) as a yellow solid. tR: 0.45 min (LC-MS 2); ESI-MS: 227 [M+H]+ (LC-MS 2); ESI-MS: 225 [M−H]− (LC-MS 2).

Workup

  1. additionThe reaction mixture was poured onto ice-water (700 mL)
  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-2dff954ca0b54a19b5193bdd040f3d44
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

Loading…