Aniline → N-phenyl-2-naphthylamine

HRID 1833960Notes

Reaction equation

HRID 1833960 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]=1O.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.P(OCCCC)(OCCCC)OCCCC>O>[C:13]1([NH:12][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 7623Tributyl phosphiteHCID 86632-Naphthol

Product 1

HCID 8679N-phenyl-2-naphthylamineYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

288 parts of β-naphthol, 250 parts of aniline and 9 parts of tributyl phosphite are mixed and fused at 130° C. At 190° C internal temperature, the reaction commences, with elimination of water. After 5 hours, the internal temperature has reached 235° C and 34 parts of water have distilled off. Thereafter, 412 parts of N-phenyl-β-naphthylamine, of melting point 100° - 102° C, distil, passing over at 230° C/15 mm Hg. This corresponds to a yield of 94% of theory.

Workup

  1. customfused at 130° C
  2. customAt 190° C internal temperature, the reaction commences
  3. customhas reached 235° C
  4. distillation34 parts of water have distilled off
  5. customThereafter, 412 parts of N-phenyl-β-naphthylamine, of melting point 100° - 102° C, distil
  6. custompassing over at 230° C/15 mm Hg

Sources & evidence

ORD record
ord-b5c7670dd8a444cdaf557949f7106f0e
Source dataset
uspto-grants-1978_01
Patent number
US04067903

Reaction notes

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