Aniline → Phenyl-1-naphthylamine

HRID 1388589Notes

Reaction equation

HRID 1388589 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](C1C=CC=CC=1)([O-])=O.[C:17]1(=O)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][CH2:18]1>CC1C=CC(C(C)C)=CC=1>[C:2]1([NH:1][C:25]2[C:26]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:22]=[CH:23][CH:24]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 7416NitrobenzeneHCID 107241-Tetralone

Product 1

HCID 7013Phenyl-1-naphthylamine

Reagents, catalysts & solvents 1

HCID 7463P-CymeneSolvent2×

Conditions

Temperature
185 °C

Procedure

To a 200 ml, 3-necked round bottom flask equipped with a thermometer and a Dean-Stark apparatus filled with p-cymene and having a condenser are added 7.45 g (80 mmole) of aniline, 4.82 g (39 mmole) of nitrobenzene, 14.6 g (100 mmole) of 1-tetralone and 65 ml of p-cymene solvent. Also introduced were catalyst and various acid promoters as indicated in Table I. The reaction mixtures were heated at reflux (about 185° C.) for 5 hours while removing the evolving water. Thereafter, the mixture was cooled to room temperature, and the catalyst was filtered out using a Celite (trademark) diatomaceous earth filter. The reaction mixture was analyzed by gas-liquid phase chromatography (GLPC) against a PANA standard. The yields mentioned in Table I are based on conversion of tetralone to PANA.

Workup

  1. customTo a 200 ml, 3-necked round bottom flask equipped with a thermometer
  2. additionAlso introduced
  3. customThe reaction mixtures
  4. temperaturewere heated
  5. customwhile removing the evolving water
  6. temperatureThereafter, the mixture was cooled to room temperature
  7. filtrationthe catalyst was filtered out
  8. filtrationfilter

Sources & evidence

ORD record
ord-c5f5ac2d786c49dd9d5f79e43040d2c8
Source dataset
uspto-grants-1984_02
Patent number
US04431841

Reaction notes

Loading…