Ammonia → 1,5-Diaminonaphthalene

HRID 1414439Notes

Reaction equation

HRID 1414439 reaction equation
[NH2:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7](S([O-])(=O)=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Na+].[NH2-:17].[Na+].N>>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([NH2:17])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24533Sodium amideHCID 236886791-Naphthalenesulfonic acid, 5-amino-, sodium salt (1:1)

Product 1

HCID 167201,5-DiaminonaphthaleneYield 89.5%

Procedure

In a 200-ml autoclave were placed 29.2 grams (0.13 mole) of anhydrous sodium 1-aminonaphthalene-5-sulfonate, 13.2 grams (0.33 mole) of sodium amide and 110 ml of liquid ammonia in the same manner as in Example 1. The resultant mixture was heated at 200° C for 5 hours. The reaction pressure in the autoclave was 180 atm. during the reaction. After the ammonia was removed, 50 ml of methanol was added to the reaction mixture for solvolysis. The product was extracted with chloroform and the chloroform was distilled off to produce crude 1,5-diaminonaphthaline. The recrystallization thereof from ether gave 18.4 grams of 1,5-diaminonaphthalene having a melting point of 187° to 189.5° C. Yield was 89.1%.

Workup

  1. customThe reaction pressure in the autoclave
  2. customduring the reaction
  3. customAfter the ammonia was removed
  4. addition50 ml of methanol was added to the reaction mixture for solvolysis
  5. extractionThe product was extracted with chloroform
  6. distillationthe chloroform was distilled off
  7. customto produce crude 1,5-diaminonaphthaline
  8. customThe recrystallization

Sources & evidence

ORD record
ord-69d45b99a0fc40fc9f1b0cd962d7106e
Source dataset
uspto-grants-1977_01
Patent number
US04001313

Reaction notes

Loading…