1,1-Dimethylhydrazine → 4-Fluoro-2-(2,2-dimethylhydrazino) nitrobenzene

HRID 1089042Notes

Reaction equation

HRID 1089042 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][N:13]([CH3:15])[NH2:14]>C(N(CC)CC)C.CO>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([NH:14][N:13]([CH3:15])[CH3:12])[CH:7]=1

Participants

5

Reactant 2

HCID 59761,1-DimethylhydrazineHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 150173004-Fluoro-2-(2,2-dimethylhydrazino) nitrobenzeneYield 48.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

10 g (0.0628 mol) of 2,4-difluoronitrobenzene was stirred for 4 days with 4.36 g (0.0728 mol) of N,N-dimethylhydrazine in 7.08 g of triethylamine and 100 ml methanol. The mixture was concentrated and the resulting solid dissolved in methylene chloride, washed with water and brine, dried with MgSO4 and concentrated to yield an orange solid. The solid was triturated in 95% ethanol/water, filtered and dried to give 6.1 g 4-fluoro-2-(2,2-dimethylhydrazino) nitrobenzene, m.p. 67°-71° C.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe resulting solid dissolved in methylene chloride
  3. washwashed with water and brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customto yield an orange solid
  7. customThe solid was triturated in 95% ethanol/water
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-3da204566d554b1097ed2a6f17a16fa1
Source dataset
uspto-grants-1990_10
Patent number
US04964895

Reaction notes

Loading…