Sodium Hydroxide → 2-Oxo-1-pyrrolidinepropanoic acid

HRID 858562Notes

Reaction equation

HRID 858562 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7]CC#N.[OH-:11].[Na+].[O:13]1[CH2:18][CH2:17]OCC1>>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:17][C:18]([OH:13])=[O:11]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 3526242-Oxo-1-pyrrolidinepropionitrile

Product 1

HCID 31466882-Oxo-1-pyrrolidinepropanoic acidYield 49%

Procedure

A solution of 2-oxo-1-pyrrolidinepropionitrile (22.4 g, 16.2 mmol), 15% NaOH solution (40 mL) and dioxane (40 mL) was heated under reflux for 5 h under N2. The reaction mixture was extracted with EtOAc. The aqueous layer was made acidic with 6N HCl amd extracted with CH2Cl2 (5×50 mL). The organic layers were dried over Na2SO4 and concentrated to give the title compound as a cream solid (12.4 g, 49%).

Workup

  1. temperatureunder reflux for 5 h under N2
  2. extractionThe reaction mixture was extracted with EtOAc
  3. extractionamd extracted with CH2Cl2 (5×50 mL)
  4. dry with materialThe organic layers were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c32affedab5246dd8e5a9d2751af7cf3
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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