Aniline → N-phenyl-2-naphthylamine

HRID 1833963Notes

Reaction equation

HRID 1833963 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1O.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.P(O)(O)O>O>[C:13]1([NH:12][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 86632-NaphtholHCID 107909Phosphorous acid

Product 1

HCID 8679N-phenyl-2-naphthylamineYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
173 °C

Procedure

288 parts of β-naphthol, 220 parts of aniline and 5 parts of phosphorous acid are mixed and heated to 173° C. At this temperature, the elimination of water commences. The reaction temperature rises to 230° C in the course of 4 hours. At that stage, the reaction has ended and 36 parts of water have been removed. The further working up is carried out as described in Example 8. 412 parts of N-phenyl-β-naphthylamine of melting point 100° - 102° C are obtained, corresponding to a yield of 94% of theory.

Workup

  1. customrises to 230° C in the course of 4 hours
  2. custom36 parts of water have been removed

Sources & evidence

ORD record
ord-9368c944081c45d3b1de18b5a0f7c263
Source dataset
uspto-grants-1978_01
Patent number
US04067903

Reaction notes

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