4-Fluoroaniline → 1-(4'Fluorophenyl) amino-2-cyano-3,4-dihydro-naphthalene

HRID 366402Notes

Reaction equation

HRID 366402 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([CH:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=O)#[N:10]>>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:19][CH2:20][C:11]=2[C:9]#[N:10])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 97314-FluoroanilineHCID 122310271-Oxo-1,2,3,4-tetrahydro-naphthalene-2-carbonitrile

Product 1

HCID 702560101-(4'Fluorophenyl) amino-2-cyano-3,4-dihydro-naphthalene

Conditions

Temperature
150 °C

Procedure

4-Fluoro-aniline (Aldrich Chemicals) (1.11 g, 10 mmol) and 2-cyano-3 ,4-dihydro-1 (2H) -naphthalenone (synthesised according to the method of Johnson. W. S. and Shelberg W. E. J. Amer. Chem. Soc., (1945), 67 p.1745.) (91.71 g 10 mmol) were heated together at 150° C. for 1 hour. After cooling, chromatography on silica with chloroform as the eluent followed by Kugelrohr distillation (175° C., 0.2 mmHg) gave the product as pale brown crystals.

Workup

  1. temperatureAfter cooling
  2. distillationchromatography on silica with chloroform as the eluent followed by Kugelrohr distillation (175° C., 0.2 mmHg)

Sources & evidence

ORD record
ord-08872a373834459ebe99fc03114d9c16
Source dataset
uspto-grants-2000_10
Patent number
US06130228

Reaction notes

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