Sodium hydride → HCID 22388484, compound

HRID 1072897Notes

Reaction equation

HRID 1072897 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[CH3:5].[H-].[Na+].[Cl:14][C:15]1[CH:22]=[C:21](F)[CH:20]=[CH:19][C:16]=1[CH:17]=[O:18]>CN(C)C=O.C(OCC)(=O)C>[Cl:14][C:15]1[CH:22]=[C:21]([O:1][CH2:2][CH2:3][N:4]([CH3:5])[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)[CH:20]=[CH:19][C:16]=1[CH:17]=[O:18]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 7374202-(N-Methyl-N-(2-pyridyl)amino)ethanol

Product 1

HCID 22388484HCID 22388484, compoundYield 44.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[N-(2-hydroxyethyl)-N-methylamino]pyridine (3.87 g) in dry N,N-dimethylformamide (39 ml) was added sodium hydride (60% in oil, 1.12 g), and the reaction mixture was stirred at room temperature for 30 min. 2-Chloro-4-fluorobenzaldehyde (4.43 g) was added to the reaction mixture and the mixture was stirred for 3 days. The mixture was diluted with ethyl acetate and washed with water. The aqueous layer was extracted twice with ethyl acetate. The organic layers were combined, dried over magnesium sulfate and concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1) to give the objective compound (3.30 g) as a pale-yellow oil.

Workup

  1. stirringthe mixture was stirred for 3 days
  2. washwashed with water
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-b319f23d428a4be6905901a5bfae8432
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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