Sodium Hydroxide → HCID 67213944, compound

HRID 1896704Notes

Reaction equation

HRID 1896704 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9].[H-].[Na+].Br[C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][N:14]=1.[OH-].[Na+]>CN1C(=O)CCC1.O>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([O:1][CH2:2][CH2:3][N:4]2[CH2:8][CH2:7][CH2:6][C:5]2=[O:9])=[N:14][CH:15]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 693532,5-DibromopyridineHCID 769801-(2-Hydroxyethyl)-2-pyrrolidinone

Product 1

HCID 67213944HCID 67213944, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

2.45 g (19 mmol) of 1-(2-hydroxyethyl)-pyrrolidin-2-one and 0.83 g (19 mmol) of sodium hydride (55% in mineral oil) in 10 ml of NMP were stirred at room temperature for 1 h. 3.0 g (12.7 mmol) of 2,5-dibromopyridine were added, and the mixture was heated to 80° C. for 2 h. Water was added, and the mixture was extracted with ethyl acetate. The combined organic phases were dried and concentrated. The remaining oil was taken up in 200 ml of tert-butyl methyl ether and treated with a solution of hydrogen chloride in diethyl ether. The resulting greasy solid was isolated by decantation of the solvent and treated with a 25% aqueous sodium hydroxide solution. The product was extracted with ethyl acetate, and the combined organic phases were dried and concentrated. Yield: 2.75 g.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe combined organic phases were dried
  3. concentrationconcentrated
  4. additiontreated with a solution of hydrogen chloride in diethyl ether
  5. customThe resulting greasy solid was isolated by decantation of the solvent
  6. extractionThe product was extracted with ethyl acetate
  7. customthe combined organic phases were dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2dd570bdb65445429d5e4ceb3f538846
Source dataset
uspto-grants-2013_08
Patent number
US08518976B2

Reaction notes

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