Acetic Acid → HCID 11449172, compound

HRID 840361Notes

Reaction equation

HRID 840361 reaction equation
C(O)(=O)C.O.CN1CCCC1=O.[Cl:13][C:14]1[C:19]([N+:20]([O-])=O)=[CH:18][C:17]([N:23]2[C:27](=[O:28])[C:26]3=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]3[C:24]2=[O:33])=[C:16]([F:34])[CH:15]=1>[Fe].O1CCCC1>[NH2:20][C:19]1[C:14]([Cl:13])=[CH:15][C:16]([F:34])=[C:17]([N:23]2[C:27](=[O:28])[C:26]3=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]3[C:24]2=[O:33])[CH:18]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 22623284HCID 22623284, compound

Product 1

HCID 11449172HCID 11449172, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 45 g of iron powder, 9 ml of acetic acid, and 36 ml of water was heated at 100° C. for 0.5 hour under stirring for activation. To the mixture was added 150 ml of N-methylpyrrolidone. The external temperature was set at 80° C., and 57.2 g of N-(4-chloro-2-fluoro-5-nitrophenyl)phthalimide was added thereto in small portions under stirring (reaction temperature: 85 to 95° C.). After completion of the addition, the stirring was continued at the same temperature for an additional 1 hour period. While the reaction mixture was warm, tetrahydrofuran was added thereto, followed by allowing the mixture to cool. Any insoluble matter was separated by Celite filtration, and the filtrate was concentrated under reduced pressure. Water was added to the concentrate, and the precipitated solid was collected by filtration. The resulting solid was washed successively with water and methanol and dried under reduced pressure to give 48.6 g of the title compound.

Workup

  1. customwas set at 80° C.
  2. stirringin small portions under stirring
  3. custom(reaction temperature: 85 to 95° C.)
  4. additionAfter completion of the addition
  5. temperatureWhile the reaction mixture was warm
  6. temperatureto cool
  7. customAny insoluble matter was separated by Celite filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. additionWater was added to the concentrate
  10. filtrationthe precipitated solid was collected by filtration
  11. washThe resulting solid was washed successively with water and methanol
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-939c3d6f192e4078befdf226c49159ea
Source dataset
uspto-grants-2002_04
Patent number
US06365753B1

Reaction notes

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