1,2-Dimethyl-3-nitrobenzene → HCID 21194232, compound

HRID 52161

Reaction equation

HRID 52161 reaction equation
[Na].[N+:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[CH3:12])([O-:4])=[O:3].[C:13](OCC)(=[O:19])[C:14]([O:16]CC)=[O:15].[OH-].[Na+]>O.C(O)C>[CH3:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([N+:2]([O-:4])=[O:3])[C:6]=1[CH2:12][C:13](=[O:19])[C:14]([OH:16])=[O:15]

Participants

7

Reactant 4

HCID 67391,2-Dimethyl-3-nitrobenzeneHCID 7268Diethyl OxalateHCID 14798Sodium HydroxideHCID 5360545Sodium

Product 1

HCID 21194232HCID 21194232, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium (3.802 g, 165.38 mmol, 2.5 eq) was added portionwise into ethanol (66 mL, 1M) at 0° C. Next, 3-nitro-ortho-xylene (10.00 g, 66.15 mmol, 1 eq) and diethyl oxalate (19.33 g, 132.23 mmol, 2 eq) were added. The mixture was stirred at room temperature for 18 hours and then refluxed for 10 minutes. 1N sodium hydroxide and water were added and the reaction was stirred for one hour. The ethanol was removed under vacuum. Water was added and the aqueous solution was acidified with concentrated hydrochloric acid to ph~2. The mixture was extracted with methylene chloride. The extracts were dried (magnesium sulfate) and concentrated to give the title compound (9.0 g, 61%).

Workup

  1. temperaturerefluxed for 10 minutes
  2. stirringthe reaction was stirred for one hour
  3. customThe ethanol was removed under vacuum
  4. additionWater was added
  5. extractionThe mixture was extracted with methylene chloride
  6. dry with materialThe extracts were dried (magnesium sulfate)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-631527924b8e4da9a6a90a47ed6c1ba9
Source dataset
uspto-grants-1997_04
Patent number
US05616591

Linked notes

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