N-Ethylaniline → HCID 19029092, compound

HRID 2255920Notes

Reaction equation

HRID 2255920 reaction equation
[Cl-].[CH3:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([CH3:10])[N+:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:18]>C(O)C>[Cl-:9].[CH3:2][C:3]1[CH:8]=[C:7]([N:19]([CH2:17][CH3:18])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[C:5]([CH3:10])[N+:4]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7670N-EthylanilineHCID 19029096HCID 19029096, compound

Product 1

HCID 19029092HCID 19029092, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,6-dimethyl-N-phenyl-4-chloropyridinium chloride (previously reported in Annalen, 1958, 617, 181-202) (2.19 g, 10 mM), N-ethylaniline (3.6 g, 30 mM) and ethanol (100 ml) was heated under reflux for 30 minutes. The solvent was removed by evaporation and the resultant syrup was purified by flash chromatography (Merck 9385 silica column, 180 g) using a 1:19 v/v mixture of methanol/methylene chloride as eluant. The resultant syrup was further purified by flash column chromatography using a neutral alumina column (ICN type N32-63, 150 g) and eluting with an increasing gradient (0-5% v/v) of methanol in dichloromethane. There was thus obtained 2,6-dimethyl-4-(N-ethylanilino)-N-phenylpyridinium chloride (1.9, 56% yield) as a pale orange glass; microanalysis, found: C,70.7; H,6.5; N,7.6; Cl,9.7%; C21H23N2Cl .H2O requires: C,70.7; H,7.0; N,7.85; Cl, 9.93%; NMR: 1.2-1.3(3H, t,CH2CH3), 2.1(6H,5 pyridine-CH3), 3.9-4.05(2H,q,CH2CH3), 6.7-7.1(2H,br, pyridine-3H and -5H), 7.35-7.7 (10H, complex, aromatic).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. customThe solvent was removed by evaporation
  4. customthe resultant syrup was purified by flash chromatography (Merck 9385 silica column, 180 g)
  5. additiona 1:19 v/v mixture of methanol/methylene chloride as eluant
  6. customThe resultant syrup was further purified by flash column chromatography
  7. washeluting with an increasing gradient (0-5% v/v) of methanol in dichloromethane

Sources & evidence

ORD record
ord-bcf0e6fd83c14a13bbe03e6cfa10b776
Source dataset
uspto-grants-1997_08
Patent number
US05654298

Reaction notes

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