2-Naphthalenecarboxaldehyde → beta-Naphthylideneaniline

HRID 917926Notes

Reaction equation

HRID 917926 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]=1C=O.[N+:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([O-])=O.[C]=O>N1C=CC=CC=1.[OH-].[Rh+3].[OH-].[OH-]>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]1=[N:13][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 62012-NaphthalenecarboxaldehydeHCID 7416NitrobenzeneHCID 178418416HCID 178418416, compound

Product 1

HCID 68129601beta-NaphthylideneanilineYield 75%

Reagents, catalysts & solvents 2

HCID 88993Rhodium hydroxide (Rh(OH)3)CatalystHCID 1049PyridineSolvent

Conditions

Temperature
170 °C

Procedure

A solution of β-naphthaldehyde (0.1 mole), nitrobenzene (0.11 mole) and rhodium hydroxide [Rh(OH)3 ] in 50 ml of pyridine were charged into a stainless steel rocking autoclave of 0.5 l capacity. The autoclave was pressurized to 140 atm with carbon monoxide and heated to 170°C for 3 hours. On completion of the reaction period, the pressure vessel was allowed to cool and the gases vented. Work-up of the reaction mixture gave 75% yield of β-naphthylideneaniline, the product being unequivocally identified by mixed melting point and spectroscopic (ir and nmr) comparison with an authentic sample.

Workup

  1. customOn completion of the reaction period
  2. temperatureto cool

Sources & evidence

ORD record
ord-1bef66ed105e4d0d88209faa9484553c
Source dataset
uspto-grants-1976_07
Patent number
US03968159

Reaction notes

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