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

HRID 1105824Notes

Reaction equation

HRID 1105824 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 tetrahydrofuran 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-f08d2d28dd994cee81a3ab3972178d37
Source dataset
uspto-grants-1982_01
Patent number
US04310527

Reaction notes

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