4-Nitrobenzamide → HCID 57465372, compound

HRID 1951579Notes

Reaction equation

HRID 1951579 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH:14]([CH3:23])[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O>CN1C(=O)CCC1>[CH3:23][C:14]1[O:9][C:8]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)=[N:10][C:15]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 120914-NitrobenzamideHCID 164522-Bromopropiophenone

Product 1

HCID 57465372HCID 57465372, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
135 °C

Procedure

a mixture of 4-nitrobenzamide (6.1 g, 37 mmol) and 2-bromopropiophenone (5.233 g, 25 mmol) in 3 mL NMP was heated to 135° C. After 2 hours at 135° C., the reaction was removed from the oil bath and ca. 30 mL of toluene was added. The resulting mixture was equilibrated to room temperature. After 15 minutes the precipitate was removed by filtration, rinsing with toluene, and discarded. The filtrate was concentrated under reduced pressure and the concentrate taken up in 50 mL ethyl acetate. A precipitate developed and was collected by filtration, rinsing the solid with ethyl acetate and drying under vacuum to afford yellow crystals (1.5 g, 22%). ESI+ m/z=281.0 [MH]+.

Workup

  1. customthe reaction was removed from the oil bath and ca. 30 mL of toluene
  2. additionwas added
  3. customwas equilibrated to room temperature
  4. customAfter 15 minutes the precipitate was removed by filtration
  5. washrinsing with toluene
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. filtrationwas collected by filtration
  8. washrinsing the solid with ethyl acetate
  9. customdrying under vacuum

Sources & evidence

ORD record
ord-40964d5df8204d5fa438098ffcbe64d4
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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