Oxalic Acid → HCID 54165010, compound

HRID 1708535Notes

Reaction equation

HRID 1708535 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]=[CH:9]N(C)C)[C:5]([Cl:13])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].C(O)(=O)C(O)=[O:19]>C(Cl)Cl.O>[Cl:13][C:5]1[CH:4]=[C:3]([N+:14]([O-:16])=[O:15])[C:2]([Cl:1])=[CH:7][C:6]=1[CH2:8][CH:9]=[O:19]

Participants

5

Reactant 2

HCID 971Oxalic AcidHCID 53750001HCID 53750001, compound

Product 1

HCID 54165010HCID 54165010, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2,5-Dichloro-4-(2-dimethylaminoethenyl)-nitrobenzene (10 g, 38.3 mmol) was dissolved in methylene chloride (200 ml) and stirred with a solution of oxalic acid (14.5 g, 115 mmol) in water (80 ml) at room temperature for 18 hours. The layers were separated and the aqueous layer extracted with methylene chloride (50 ml). The combined organic layers were washed with water and brine, dried over magnesium sulfate and filtered. The solution was evaporated to yield the title compound. NMR (CDCl3) δ 9.70 (s, 1), 8.01 (s, 1), 7.49 (s, 1), 3.98 (s, 2).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer extracted with methylene chloride (50 ml)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe solution was evaporated

Sources & evidence

ORD record
ord-36fbd0bb9cda4b1eade419857dcba389
Source dataset
uspto-grants-1994_10
Patent number
US05359068

Reaction notes

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