Aniline → Phenyl-1-naphthylamine

HRID 1833965Notes

Reaction equation

HRID 1833965 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-])(OCC1C=CC=CC=1)OCC1C=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 21904359Dibenzylphosphite

Product 1

HCID 7013Phenyl-1-naphthylamineYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
195 °C

Procedure

288 parts of α-naphthol, 205 parts of aniline and 10 parts of dibenzyl phosphite are mixed and heated to 195° C. The elimination of water commences at this temperature and has ended when the internal temperature is 235° C. 33 parts of water are removed in the course of 4 hours. After distilling off excess α-naphthol and aniline, 374 parts of phenyl-α-naphthylamine, boiling at 202° - 204° C/5 mm Hg, are obtained; 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. custom33 parts of water are removed in the course of 4 hours
  3. distillationAfter distilling off excess α-naphthol and aniline, 374 parts of phenyl-α-naphthylamine, boiling at 202° - 204° C/5 mm Hg
  4. customare obtained

Sources & evidence

ORD record
ord-b2590d62f983472885107e8adf772c58
Source dataset
uspto-grants-1978_01
Patent number
US04067903

Reaction notes

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