Water → 1,5-Diaminonaphthalene

HRID 2399093Notes

Reaction equation

HRID 2399093 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[C:9]([N+:14]([O-])=O)[CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)([O-])=O.O.[H][H]>NC1C=CC=CC=1.[Pd]>[NH2:1][C:4]1[C:13]2[C:8](=[C:9]([NH2:14])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 118031,5-DinitronaphthaleneHCID 178418361HCID 178418361, compound4×

Product 1

HCID 167201,5-DiaminonaphthaleneYield 55.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6115AnilineSolvent

Conditions

Temperature
20 °C

Procedure

60 g (0.275 mol) of 1,5-dinitro naphthalene were suspended, in a 700 ml stirrer autoclave, in 340 ml of aniline and treated with 8 g of water-moist, 5% strength catalyst of palladium on activated charcoal, corresponding to 2.8 g of dry catalyst. Hydrogenation was performed at a temperature of about 100° C. and an initial hydrogen pressure of about 10 bars. As soon as the hydrogen pressure dropped to 5 bars, the hydrogen supply was stepped up until the original value of 10 bars was reattained. After 104 minutes the hydrogen uptake was finished and the reaction over. The catalyst was separated off at about 70° C. by filtration and the filtrate cooled to 20° C. whereupon 1,5-diamino naphthalene crystallized out. The crystallate was then filtered off and washed twice with 50 ml of methanol; 24 g of 1,5-diamino naphthalene were obtained with a m.p. of 189°-190° C.

Workup

  1. customwas performed at a temperature of about 100° C.
  2. customthe reaction over
  3. customThe catalyst was separated off at about 70° C. by filtration
  4. customcrystallized out
  5. filtrationThe crystallate was then filtered off
  6. washwashed twice with 50 ml of methanol

Sources & evidence

ORD record
ord-6854e970db9242078559e2e9f45358fe
Source dataset
uspto-grants-1977_05
Patent number
US04026944

Reaction notes

Loading…