Ammonia → 2-Naphthylamine

HRID 1414437Notes

Reaction equation

HRID 1414437 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1S([O-])(=O)=O.[Na+].[NH2-:16].[Na+].N>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH2:16]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24533Sodium amideHCID 23661868Sodium 2-naphthalenesulfonate

Product 1

HCID 70572-NaphthylamineYield 85.7%

Procedure

In a 200-ml autoclave were placed 27.4 grams (0.119 mole) of anhydrous sodium 2-naphthalene sulfonate, 10 grams (0.25 mole) of sodium amide and 80 ml of liquid ammonia in the same manner as in Example 1. The resultant mixture was heated at 120° C for 10 hours. The reaction pressure in the autoclave was 90 atm. during the reaction. After the ammonia was removed, 15 ml of water was added to the reaction mixture for hydrolysis. The product was extracted with ether and the ether was distilled off to produce crude 2-naphthylamine. Recrystallization from methanol gave 14.6 grams of 2-naphthylamine having a melting point of 111° to 112° C. Yield was 85.7%.

Workup

  1. customThe reaction pressure in the autoclave
  2. customduring the reaction
  3. customAfter the ammonia was removed
  4. addition15 ml of water was added to the reaction mixture for hydrolysis
  5. extractionThe product was extracted with ether
  6. distillationthe ether was distilled off
  7. customto produce crude 2-naphthylamine
  8. customRecrystallization from methanol

Sources & evidence

ORD record
ord-54853af1400d427da30b378c2f55bd87
Source dataset
uspto-grants-1977_01
Patent number
US04001313

Reaction notes

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