Sodium hydride → 2-[2-(4-Chlorophenyl)ethoxy]-5-nitropyridine

HRID 1995815Notes

Reaction equation

HRID 1995815 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][OH:10])=[CH:6][CH:5]=1.Cl[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1>CS(C)=O>[Cl:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][O:10][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74647p-Chlorophenethylic alcoholHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 204861162-[2-(4-Chlorophenyl)ethoxy]-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred mixture of NaH (0.77 g) and DMSO is slowly added 4-chlorophenethyl alcohol (5 g) in DMSO (20 ml) while maintaining the temperature at or below 32°. After gas evolution stops, 2-chloro-5-nitropyridine (4 g) is added in small portions while maintaining temperature below 25°. After stirring about 1 hour, the reaction is poured onto about 300 g ice and then filtered. The solid is dissolved in ether, washed with water, dried (sodium sulfate) and solvent evaporated to give 2-(4-chlorophenethoxy)-5-nitropyridine, a grey solid.

Workup

  1. temperaturewhile maintaining the temperature at or below 32°
  2. temperaturewhile maintaining temperature below 25°
  3. filtrationfiltered
  4. dissolutionThe solid is dissolved in ether
  5. washwashed with water
  6. dry with materialdried (sodium sulfate) and solvent
  7. customevaporated

Sources & evidence

ORD record
ord-9a3fff46a8c445a0aa92c654f3f26c3e
Source dataset
uspto-grants-1983_09
Patent number
US04406690

Reaction notes

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