Dimethyl Sulfoxide → HCID 67371284, compound

HRID 1678138Notes

Reaction equation

HRID 1678138 reaction equation
[CH2:1]([O:8][C:9](=[O:30])[CH:10]([C:21]1[CH:26]=[CH:25][N:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28])C(OCC1C=CC=CC=1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Li+].CS(C)=O>O>[CH2:1]([O:8][C:9](=[O:30])[CH2:10][C:21]1[CH:26]=[CH:25][N:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 433294Lithium ChlorideHCID 11603852HCID 11603852, compound

Product 1

HCID 67371284HCID 67371284, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The title compound is prepared following the procedures of WO, 00 55159 as follows. A solution of 2-(3-nitropyridin-4-yl)malonic acid dibenzyl ester (1.58 g, 5.6 mmol), lithium chloride (250 mg, 10.6 mmol), dimethylsulfoxide (35 mL) and water (95 mL) is heated at reflux for 8 hr. After cooling to room temperature, the reaction is diluted with water and extracted with ethyl acetate. The combined extract is extracted with water, with brine, dried, filtered and concentrated to yield (3-nitropyridin-4-yl)acetic acid benzyl ester (1.13 g, 99% yield) as a yellow-orange oil. The material is purified by chromatography eluting with pentane-20 to 30% ethyl acetate to afford the product as a pink oil. MS 273 (M+H).

Workup

  1. customThe title compound is prepared
  2. temperatureat reflux for 8 hr
  3. extractionextracted with ethyl acetate
  4. extractionThe combined extract
  5. extractionis extracted with water, with brine
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7db6fcbe93604e3980be49d85c395daa
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

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