Hydrazine hydrate (1:1) → HCID 12901513, compound

HRID 1391054Notes

Reaction equation

HRID 1391054 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:6]=1[NH:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:2]=[CH2:3].O.NN>[Ni].O1CCCC1>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[C:6]=1[NH:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 20555088HCID 20555088, compound

Product 1

HCID 12901513HCID 12901513, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 0.5 g of Raney nickel in 50 ml of tetrahydrofurane is warmed to 50°, whilst stirring, and a solution of 10.0 g of 1-allyloxy-2-butylamino-3-nitrobenzene and 10 ml of hydrazine hydrate in 100 ml of tetrahydrofurane is added dropwise in the course of 40 minutes. The reaction mixture is then heated to the boil for 1 hour, whilst stirring and under reflux. After cooling, the catalyst is filtered off, the filtrate is evaporated under reduced pressure and the oily residue is subjected to distillation in a bulb tube, 1-allyloxy-2-butylamino-3-aminobenzene being obtained at 100°/0.1 mm Hg (external temperature) as a yellowish distillate.

Workup

  1. temperatureis warmed to 50°
  2. temperatureThe reaction mixture is then heated to the boil for 1 hour
  3. stirringwhilst stirring
  4. temperatureunder reflux
  5. temperatureAfter cooling
  6. filtrationthe catalyst is filtered off
  7. customthe filtrate is evaporated under reduced pressure
  8. distillationthe oily residue is subjected to distillation in a bulb tube

Sources & evidence

ORD record
ord-545656127741461386e84d39b1f1410b
Source dataset
uspto-grants-1979_02
Patent number
US04140789

Reaction notes

Loading…