Aniline → Phenyl-1-naphthylamine

HRID 1833949Notes

Reaction equation

HRID 1833949 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.C1(OP(OC2C=CC=CC=2)OC2C=CC=CC=2)C=CC=CC=1>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 7540Triphenyl phosphite

Product 1

HCID 7013Phenyl-1-naphthylamineYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

144 parts of α-naphthol, 150 parts of aniline and 5 parts of triphenylphosphite are mixed and first heated to 180° C. The reaction commences, with elimination of water. The water is removed by means of a water separator and the aniline evolved is returned. The temperature rises to 210° in the course of 4 hours. After a further 4 hours at 212° C, the elimination of water has ended (18 parts of H2O). The reaction mixture is cooled to 150° C and the excess aniline is distilled off under reduced pressure. Thereafter, 208 parts of phenyl-α-naphthylamine distil at 202° - 203° C/5 mm Hg; this product has a melting point of 55° - 58° C and corresponds to a yield of 95% of theory.

Workup

  1. customThe reaction commences
  2. customThe water is removed by means of a water separator
  3. customrises to 210° in the course of 4 hours
  4. temperatureThe reaction mixture is cooled to 150° C
  5. distillationthe excess aniline is distilled off under reduced pressure
  6. customThereafter, 208 parts of phenyl-α-naphthylamine distil at 202° - 203° C/5 mm Hg

Sources & evidence

ORD record
ord-8028dd6339274769a0d7f3dcb6e1a10f
Source dataset
uspto-grants-1978_01
Patent number
US04067903

Reaction notes

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