Morpholine → HCID 66638735, compound

HRID 1094992Notes

Reaction equation

HRID 1094992 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([NH:10][C:11](=[O:16])[CH2:12][CH2:13][CH2:14]Cl)[CH:7]=[CH:6][C:5]=1[N+:17]([O-:19])=[O:18].N1CCOCC1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:16])[CH:7]=[CH:6][C:5]=1[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 66638736HCID 66638736, compound

Product 1

HCID 66638735HCID 66638735, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Subsequently, 5-(4-chloro-butyrylamino)-2-nitro-benzoic acid methyl ester (50 mg) was dissolved in N,N-dimethylformamide (5 ml). Morpholine (70 mg) and potassium carbonate (44 mg) were added to the solution at room temperature, and the mixture was stirred at room temperature for 3 hr. After the completion of the reaction, distilled water was added thereto at room temperature, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 2-nitro-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (45 mg, yield 100%).

Workup

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionat room temperature, and the mixture was subjected to separatory extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialwas dried over sodium sulfate
  7. concentrationwas then concentrated under the reduced pressure
  8. customThe residue was purified by column chromatography
  9. washeluted with a chloroform-methanol system

Sources & evidence

ORD record
ord-2bd907268a6a4fc4b0d50e0d86239345
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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