Aniline → Phenyl-1-naphthylamine

HRID 1833958Notes

Reaction equation

HRID 1833958 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([O-])(OCC)OCC>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 3780918Diethylphosphite

Product 1

HCID 7013Phenyl-1-naphthylamineYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
196 °C

Procedure

288 parts of α-naphthol, 205 parts of aniline and 10 parts of diethyl phosphite are mixed and heated to 196° C. The elimination of water commences at this temperature and has ended when the internal temperature is 234° C. 27 parts of water are removed in the course of 8 hours. After distilling off excess α-naphthol and aniline, 330 parts of phenyl-α-naphthylamine are obtained at a boiling point of 203° - 205° C/5 mm Hg; the product has a melting point of 54° - 58° C and corresponds to a yield of 75% of theory.

Workup

  1. customis 234° C
  2. custom27 parts of water are removed in the course of 8 hours
  3. distillationAfter distilling off excess α-naphthol and aniline, 330 parts of phenyl-α-naphthylamine
  4. customare obtained at a boiling point of 203° - 205° C/5 mm Hg

Sources & evidence

ORD record
ord-8bca758f1b3b4d2d9f186fbaa4cbb1af
Source dataset
uspto-grants-1978_01
Patent number
US04067903

Reaction notes

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