Aniline → Phenyl-1-naphthylamine

HRID 1833955Notes

Reaction equation

HRID 1833955 reaction equation
[C:1]1(O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[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:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 70051-NaphtholHCID 7623Tributyl phosphite

Product 1

HCID 7013Phenyl-1-naphthylamineYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
196 °C

Procedure

288 parts of α-naphthol, 205 parts of aniline and 10 parts of tributyl phosphite are mixed and first heated to 196° C. The reaction commences, with elimination of water. The water is removed by means of a water separator and the aniline which has escaped is returned. The internal temperature is raised to 235° C in the course of 8 hours. At this point, the elimination of water has ended (33 parts of water). The reaction mixture is cooled to 150° C and the excess aniline and α-naphthol are distilled off under reduced pressure. Thereafter, 400 parts of phenyl-α-naphthylamine are obtained at a boiling point of 202° - 203° C/5 mm Hg; the product has a melting point of 55° - 58° C and corresponds to a yield of 91% of theory.

Workup

  1. customThe reaction commences
  2. customThe water is removed by means of a water separator
  3. temperatureThe internal temperature is raised to 235° C in the course of 8 hours
  4. temperatureThe reaction mixture is cooled to 150° C
  5. distillationthe excess aniline and α-naphthol are distilled off under reduced pressure

Sources & evidence

ORD record
ord-84760c3dcc68400998eea5e6f71405bd
Source dataset
uspto-grants-1978_01
Patent number
US04067903

Reaction notes

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