Aniline → Phenyl-1-naphthylamine

HRID 1833957Notes

Reaction equation

HRID 1833957 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-])(OC1C=CC=CC=1)OC1C=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 23418553Diphenoxyphosphanolate

Product 1

HCID 7013Phenyl-1-naphthylamineYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
197 °C

Procedure

288 parts of α-naphthol, 205 parts of aniline and 10 parts of diphenyl phosphite are mixed and heated to 197° C. The elimination of water commences at this temperature and has ended when the internal temperature is 235° C. 31 parts of water are removed in the course of 8 hours. After distilling off excess α-naphthol and aniline, 372 parts of phenyl-α-naphthylamine are obtained at a boiling point of 202° - 204° C/5 mm Hg; the product has a melting point of 55° - 58° C and corresponds to a yield of 85% of theory.

Workup

  1. customis 235° C
  2. custom31 parts of water are removed in the course of 8 hours
  3. distillationAfter distilling off excess α-naphthol and aniline, 372 parts of phenyl-α-naphthylamine
  4. customare obtained at a boiling point of 202° - 204° C/5 mm Hg

Sources & evidence

ORD record
ord-42755be7d4cf4d58b23d741410ba3560
Source dataset
uspto-grants-1978_01
Patent number
US04067903

Reaction notes

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