Methylhydrazine → 4-Bromo-1,2-dihydro-1-methyl-3,6-pyridazinedione

HRID 919306Notes

Reaction equation

HRID 919306 reaction equation
[Br:1][C:2]1[C:3](=O)[O:4][C:5](=[O:7])[CH:6]=1.[CH3:9][NH:10][NH2:11]>CC(O)=O>[Br:1][C:2]1[C:3](=[O:4])[NH:11][N:10]([CH3:9])[C:5](=[O:7])[CH:6]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 800273-Bromo-2,5-furandione

Product 1

HCID 901770424-Bromo-1,2-dihydro-1-methyl-3,6-pyridazinedione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-bromofuran-2,5-dione (100 g, 0.565 mol) in HOAc (1.0 L) cooled in an ice-water bath, 40% aq. methylhydrazine solution (65 g, 0.565 mol) was added dropwise while the internal temperature was held below 20° C. The mixture was allowed to warm to room temperature and stirred for 16 h. The precipitated solid was collected by filtration, washed with EtOAc, and dried in vacuo to give desired product as a white solid: LC/MS m/z=206.9 (M+H)+; 1H NMR (400 MHz, CD3OD) δ: 7.35 (s, 1 H), 3.60 (s, 3 H).

Workup

  1. customwas held below 20° C
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with EtOAc
  4. customdried in vacuo

Sources & evidence

ORD record
ord-829960a92b484f6ea9a641190e671ce5
Source dataset
uspto-grants-2016_03
Patent number
US09273033B2

Reaction notes

Loading…