N-Methylaniline → 5-(3,4-dimethoxybenzoyl)-2-(N-methylanilino)pyridine

HRID 1031500Notes

Reaction equation

HRID 1031500 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].[Na+].Cl[C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:29])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=2)=[CH:14][N:13]=1>CN(C)C=O>[CH3:28][O:27][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[O:25][CH3:26])[C:18]([C:15]1[CH:16]=[CH:17][C:12]([N:2]([CH3:1])[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[N:13][CH:14]=1)=[O:29]

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 24758Sodium hydrideHCID 148232212-Chloro-5-(3,4-dimethoxybenzoyl)pyridine

Product 1

HCID 148788655-(3,4-dimethoxybenzoyl)-2-(N-methylanilino)pyridineYield 31.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In dimethylformamide (30 ml) was dissolved N-methylaniline (1.2 g). To the solution was added 60% sodium hydride (dispersion in praraffin) (150 mg), and the mixture was stirred for 30 minutes. Then there was added 2-chloro-5-(3,4-dimethoxybenzoyl)pyridine (500 mg). The mixture was stirred for 4 hours at 90° C. The reaction mixture was poured into ice-water, which was subjected to extraction with dichloromethane. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The concentrate was purified by means of a silica gel column chromatography (eluent: n-hexane +ethyl acetate=2:1) to obtain 5-(3,4-dimethoxybenzo-yl)-2-(N-methylanilino)pyridine (200 mg) as an oil.

Workup

  1. stirringThe mixture was stirred for 4 hours at 90° C
  2. extractionwas subjected to extraction with dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe concentrate was purified by means of a silica gel column chromatography (eluent: n-hexane +ethyl acetate=2:1)

Sources & evidence

ORD record
ord-3cbcb446ba4046c6aa34102311824f6f
Source dataset
uspto-grants-1990_09
Patent number
US04954497

Reaction notes

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