Ammonia → 1,5-Diaminonaphthalene

HRID 1414436Notes

Reaction equation

HRID 1414436 reaction equation
[C:1]1(S([O-])(=O)=O)[C:10]2[CH:9]=[CH:8][CH:7]=[C:6](S([O-])(=O)=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Na+].[Na+].[NH2-:21].[Na+].[NH3:23]>>[NH2:21][C:1]1[C:10]2[C:5](=[C:6]([NH2:23])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24533Sodium amideHCID 74248Disodium 1,5-naphthalenedisulfonate

Product 1

HCID 167201,5-DiaminonaphthaleneYield 84.5%

Procedure

In a 200-ml autoclave were placed 26.6 grams (0.08 mole) of anhydrous sodium 1,5-naphthalene disulfonate, 17.6 grams (0.44 mole) of sodium amide and 80 ml of liquid ammonia in the same manner as in Example 1. The resultant mixture was heated at 180° C for 10 hours. The reaction pressure in the autoclave was 160 atm. during the reaction. After the ammonia was removed 30 ml of methanol was added to the reaction mixture for solvolysis. Thereafter the product was treated in the same manner as in Example 2, whereby 10.7 grams of 1,5-diaminonaphthalene was obtained. Yield was 84.5%.

Workup

  1. customThe reaction pressure in the autoclave
  2. customduring the reaction
  3. customAfter the ammonia was removed 30 ml of methanol
  4. additionwas added to the reaction mixture for solvolysis
  5. additionThereafter the product was treated in the same manner as in Example 2

Sources & evidence

ORD record
ord-70e0eb62538d40efac5979c168e51986
Source dataset
uspto-grants-1977_01
Patent number
US04001313

Reaction notes

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