Lithium Chloride → HCID 59378012, compound

HRID 2065741Notes

Reaction equation

HRID 2065741 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]([C:11]1[CH:16]=[C:15]([NH2:17])[C:14]([CH3:18])=[CH:13][C:12]=1[Cl:19])C(OCC)=O)[CH3:2].[Cl-].[Li+]>CS(C)=O.O>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:11]1[CH:16]=[C:15]([NH2:17])[C:14]([CH3:18])=[CH:13][C:12]=1[Cl:19])[CH3:2]

Participants

5

Reactant 2

HCID 433294Lithium ChlorideHCID 59377985HCID 59377985, compound

Product 1

HCID 59378012HCID 59378012, compoundYield 50.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
170 °C

Procedure

To a solution of 2-(5-amino-2-chloro-4-methyl-phenyl)-malonic acid diethyl ester (0.50 g, 2.17 mmol) in DMSO (3 ml) and water (0.078 ml) was added, followed by lithium chloride (0.138 g, 3.26 mmol). The mixture was heated to 170° C. for three hours, then cooled to room temperature. Water was added and the mixture was extracted with EtOAc. The combined extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the crude product by flash chromatography (hexanes:EtOAc 8:2) gave 0.250 g (50%) of (5-amino-2-chloro-4-methyl-phenyl)-acetic acid ethyl ester as a white foam.

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification of the crude product by flash chromatography (hexanes:EtOAc 8:2)

Sources & evidence

ORD record
ord-ef8441fe26b44e5fbfc83219bea32b1d
Source dataset
uspto-grants-2012_10
Patent number
US08288552B2

Reaction notes

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