Water → HCID 25120490, compound

HRID 2359464Notes

Reaction equation

HRID 2359464 reaction equation
[H-].[Na+].[C:3]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:4][OH:5].Cl[C:11]1[C:16]([CH3:17])=[CH:15][C:14]([N+:18]([O-:20])=[O:19])=[CH:13][N:12]=1.O>O1CCCC1>[CH3:17][C:16]1[C:11]([O:5][CH2:4][C:3]([O:7][CH2:8][CH3:9])=[O:6])=[N:12][CH:13]=[C:14]([N+:18]([O-:20])=[O:19])[CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12184Ethyl GlycolateHCID 24758Sodium hydrideHCID 896482-Chloro-3-methyl-5-nitropyridine

Product 1

HCID 25120490HCID 25120490, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Sodium hydride (116 mg: 60%) was suspended in tetrahydrofuran (4 mL). While the suspension was cooled on ice, ethyl glycolate (273 μL) was added. The mixture was stirred at room temperature (20 to 30° C.) for 30 min. Subsequently, 2-chloro-3-methyl-5-nitropyridine (200 mg) was added to the mixture portionwise at room temperature (20 to 30° C.) and the mixture was stirred at room temperature (20 to 30° C.) for 3 hours. Water was then added to the reaction mixture and the mixture was extracted twice with chloroform. The organic layer was concentrated under reduced pressure to afford 310 mg of the crude desired product of Compound 19 as a brown amorphous.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature (20 to 30° C.) for 3 hours
  3. extractionthe mixture was extracted twice with chloroform
  4. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7977c95e8d2a4f26bb23d78a5a823f4d
Source dataset
uspto-grants-2014_04
Patent number
US08685989B2

Reaction notes

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