Ethanol → 2-Naphthylamine

HRID 2306870Notes

Reaction equation

HRID 2306870 reaction equation
Cl.Cl.[C:3]1(NCCN)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.C(O)C.C(=O)([O-])[O-].[K+].[K+].[N+:26](C1C=C([N+]([O-])=O)C=CC=1F)([O-])=O>O.[OH-].[Na+]>[CH:4]1[CH:5]=[CH:6][C:7]2[CH:8]=[C:9]([NH2:26])[CH:10]=[CH:11][C:12]=2[CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 6264DinitrofluorobenzeneHCID 11430Potassium CarbonateHCID 15106N-1-Naphthylethylenediamine dihydrochloride

Product 1

HCID 70572-Naphthylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

10.0 g (38.6 mmoles) of N-(1-naphthyl)-ethylenediamine dihydrochloride were dissolved in a little water and neutralized with dilute sodium hydroxide solution. After the addition of 120 ml of ethanol and 6.4 g of potassium carbonate (46.3 mmoles), 7.2 g (38.7 mmoles) of 2,4-dinitrofluorobenzene were added dropwise. After refluxing for 1 hour, the whole was cooled to room temperature and the deposit was filtered off under suction and washed with water/ethanol. The intermediate product (2-(2,4-dinitrophenyl)-amino)-ethyl)-naphthylamine was obtained in the form of red crystals with a melting point of 263° C.

Workup

  1. additionwere added dropwise
  2. temperatureAfter refluxing for 1 hour
  3. filtrationthe deposit was filtered off under suction
  4. washwashed with water/ethanol

Sources & evidence

ORD record
ord-d6b9a224570e4d0eb3409899f20c935a
Source dataset
uspto-grants-2004_12
Patent number
US06828443B1

Reaction notes

Loading…