4-Nitrobenzoyl chloride → HCID 136005808, compound

HRID 915970Notes

Reaction equation

HRID 915970 reaction equation
CS(O)(=O)=O.[CH:6]1([C:12]2[C:20]3[C:19](=[O:21])[NH:18][C:17]([C:22]4[CH:27]=[CH:26][C:25]([N:28]5CCC(O)CC5)=[CH:24][C:23]=4OC)=[N:16][C:15]=3[N:14]([CH3:37])[N:13]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[N+](C1C=CC(C(Cl)=O)=CC=1)([O-])=O>N1C=CC=CC=1>[NH2:28][C:25]1[CH:26]=[CH:27][C:22]([C:17]2[NH:18][C:19](=[O:21])[C:20]3[C:12]([CH:6]4[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]4)=[N:13][N:14]([CH3:37])[C:15]=3[N:16]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 136333294HCID 136333294, compound

Product 1

HCID 136005808HCID 136005808, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a pyridine solution of 2.2 g (10 mmol) of the compound obtained in Example 32, 2.2 g (13 mmol) of p-nitrobenzoyl chloride was added, and the mixture was stirred at room temperature for 1.5 hours. Then, the reaction mixture was distilled under reduced pressure, and an aqueous solution of sodium hydrogen carbonate was added to the residue, followed by extracting the mixture with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate, followed by distilling off the solvent under reduced pressure. To the residue, 30 ml of methanol and 400 mg of 10% palladium carbon were added. The mixture was stirred for 8 hours in an atmosphere of hydrogen at room temperature and atmospheric pressure. Then, the catalyst was removed by filtration, and the filtrate was distilled under reduced pressure. To the residue, 80 ml of ethanol and 40 ml of a 1M aqueous solution of sodium hydroxide were added, followed by heating the mixture under reflux for 5 hours. Then, the reaction mixture was cooled to room temperature, diluted with water, and extracted with chloroform. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=30/1) to obtain 960 mg (30%) of the captioned compound.

Workup

  1. distillationThen, the reaction mixture was distilled under reduced pressure
  2. additionan aqueous solution of sodium hydrogen carbonate was added to the residue
  3. extractionby extracting the mixture with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate
  6. distillationby distilling off the solvent under reduced pressure
  7. additionTo the residue, 30 ml of methanol and 400 mg of 10% palladium carbon were added
  8. stirringThe mixture was stirred for 8 hours in an atmosphere of hydrogen at room temperature
  9. customThen, the catalyst was removed by filtration
  10. distillationthe filtrate was distilled under reduced pressure
  11. additionTo the residue, 80 ml of ethanol and 40 ml of a 1M aqueous solution of sodium hydroxide were added
  12. temperatureby heating the mixture
  13. temperatureunder reflux for 5 hours
  14. temperatureThen, the reaction mixture was cooled to room temperature
  15. additiondiluted with water
  16. extractionextracted with chloroform
  17. washThe organic layer was washed with water
  18. dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate
  19. distillationby distilling off the solvent under reduced pressure
  20. customThe residue was purified by silica gel column chromatography (chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-41c40afeca9046ca91532b5780d9d386
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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