1-Naphthol → N-(4-Ethoxyphenyl)naphthalen-1-amine

HRID 1833962Notes

Reaction equation

HRID 1833962 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.[CH3:12][CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=1.P(OCC1C=CC=CC=1)(OCC1C=CC=CC=1)OCC1C=CC=CC=1>O>[CH2:13]([O:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][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:19][CH:20]=1)[CH3:12]

Participants

5

Reactant 3

HCID 70051-NaphtholHCID 90764-EthoxyanilineHCID 11810300Tribenzyl phosphite

Product 1

HCID 80716N-(4-Ethoxyphenyl)naphthalen-1-amineYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
218 °C

Procedure

288 parts of α-naphthol, 411 parts of p-phenetidine and 8 parts of tribenzyl phosphite are mixed and heated to 218° C. At this temperature, the elimination of water commences. The reaction temperature rises to 250° C in the course of 10 hours. At that stage, the reaction has ended and 36 parts of water have been removed. After removing excess p-phenetidine, the N-p-ethoxy-phenyl-α-naphthylamine distils at a boiling point of 233° - 235° C/5 mm Hg. 479 parts of end product of melting point 72° - 75° C are obtained. This corresponds to a yield of 91% of theory.

Workup

  1. customrises to 250° C in the course of 10 hours
  2. custom36 parts of water have been removed
  3. customAfter removing excess p-phenetidine
  4. customthe N-p-ethoxy-phenyl-α-naphthylamine distils at a boiling point of 233° - 235° C/5 mm Hg
  5. custom479 parts of end product of melting point 72° - 75° C are obtained

Sources & evidence

ORD record
ord-572ccf88eb2c4232a6112045d42139fd
Source dataset
uspto-grants-1978_01
Patent number
US04067903

Reaction notes

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