Water → Ethyl 4-Cyano-2-nitrophenylacetate

HRID 1386340Notes

Reaction equation

HRID 1386340 reaction equation
[Cl-].[Li+].O.[C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12](C(OCC)=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]([N+:23]([O-:25])=[O:24])[CH:7]=1)#[N:5]>CS(C)=O>[C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]([N+:23]([O-:25])=[O:24])[CH:7]=1)#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 53993532HCID 53993532, compound

Product 1

HCID 21717235Ethyl 4-Cyano-2-nitrophenylacetateYield 91.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

Lithium chloride (10.7 g, 255 mmol) and water (2.3 g, 127 mmol) were added to a solution of diethyl (4-cyano-2-nitrophenyl)malonate (39 g, 127 mmol) in DMSO (700 ml) under argon and the solution was heated at 100° C. for 4 hours. The reaction mixture was allowed to cool and then poured slowly into stirred ice water (1000 ml). The resulting pale yellow precipitate was colllected by filtration, washed with water (100 ml×4) and dried under vacuum to give ethyl (4-cyano-2-nitrophenyl)acetate (27.1 g, 91%).

Workup

  1. temperatureto cool
  2. additionpoured slowly
  3. filtrationThe resulting pale yellow precipitate was colllected by filtration
  4. washwashed with water (100 ml×4)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-5494ee127f9b46a6b579556e30b7b4a2
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

Loading…