2-Chloro-5-nitrobenzoic acid → HCID 881114, compound

HRID 1458712Notes

Reaction equation

HRID 1458712 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH:14]1[N:18]=[CH:17][N:16]([C:19](N2C=NC=C2)=O)[CH:15]=1>C1COCC1.CN(C)CCN>[CH3:17][N:16]([CH2:15][CH2:14][NH:18][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=1[Cl:1])[CH3:19]

Participants

5

Reactant 2

HCID 172872-Chloro-5-nitrobenzoic acidHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 881114HCID 881114, compoundYield 73,610.602%

Reagents, catalysts & solvents 2

HCID 66053N,N-DimethylethylenediamineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10 g (0.050 mmol) of 2-chloro-5-nitrobenzoic acid in 60 ml of THF was cooled over an ice bath, followed by the addition of 10 g (0.064 mmol) of CDI. The thus-obtained mixture was stirred at room temperature for 1 hour. To the solution, 12 ml (0.11 mmol) of N,N-dimethylethylenediamine were added dropwise, followed by stirring at room temperature for 3 hours. After the solvent was distilled out, the residue was dissolved in ethyl acetate. After the solution so obtained was washed with a 10% aqueous solution of sodium hydrogencarbonate, magnesium sulfate was added to the solution to dry the same. The ethyl acetate was distilled out under reduced pressure and the residue was purified by chromatography on a silica gel column (ethyl acetate), whereby 10 g of the title compound were obtained as a colorless oil (yield: 74%).

Workup

  1. stirringby stirring at room temperature for 3 hours
  2. distillationAfter the solvent was distilled out
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. customAfter the solution so obtained
  5. washwas washed with a 10% aqueous solution of sodium hydrogencarbonate, magnesium sulfate
  6. additionwas added to the solution
  7. customto dry the same
  8. distillationThe ethyl acetate was distilled out under reduced pressure
  9. customthe residue was purified by chromatography on a silica gel column (ethyl acetate)

Sources & evidence

ORD record
ord-f99a8788bdbb438c9321f54a6358744e
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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