Lithium Hydroxide → 4-(5-Nitropyridin-2-yl)butanenitrile

HRID 1504964Notes

Reaction equation

HRID 1504964 reaction equation
[C:1]([CH2:3][CH2:4][C:5]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1)(C(OC)=O)C(OC)=O)#[N:2].[Li+].[OH-]>CO.O>[N+:20]([C:17]1[CH:18]=[CH:19][C:14]([CH2:5][CH2:4][CH2:3][C:1]#[N:2])=[N:15][CH:16]=1)([O-:22])=[O:21]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68292301HCID 68292301, compound

Product 1

HCID 682920074-(5-Nitropyridin-2-yl)butanenitrileYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of compound 76 (3.3 g, 10.7 mmol) in CH3OH (100 mL) was added a solution of LiOH (15.4 g, 64.2 mmol) in H2O (100 mL) at room temperature with stirring. The mixture was stirred at room temperature for 2 h. Methanol was removed in vacuo and the residual aqueous solution was washed with EtOAc (two times), then was acidified to pH=2 with 1N HCl. The aqueous phase was extracted with EtOAc. The combined organic extract was dried over Na2SO4, then was stirred at 50° C. for overnight. The solution was concentrated to afford compound 77 (1.9 g, 95%) as a yellow oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 h
  2. customMethanol was removed in vacuo
  3. washthe residual aqueous solution was washed with EtOAc (two times)
  4. extractionThe aqueous phase was extracted with EtOAc
  5. extractionThe combined organic extract
  6. dry with materialwas dried over Na2SO4
  7. stirringwas stirred at 50° C. for overnight
  8. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-c09be9ae0b944f12b24d89018c9765c8
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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