Pentamethylbenzene → HCID 17856978, compound

HRID 1784895Notes

Reaction equation

HRID 1784895 reaction equation
C([O:8][C:9]1[C:10]([N+:25]([O-:27])=[O:26])=[C:11]([CH:22]=[CH:23][CH:24]=1)[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][N:16]=1)=[O:13])C1C=CC=CC=1.CC1C(C)=C(C)C(C)=C(C)C=1>FC(F)(F)C(O)=O>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:12](=[O:13])[C:11]2[CH:22]=[CH:23][CH:24]=[C:9]([OH:8])[C:10]=2[N+:25]([O-:27])=[O:26])=[N:16][CH:17]=1

Participants

4

Reactant 2

HCID 12784PentamethylbenzeneHCID 17856970HCID 17856970, compound

Product 1

HCID 17856978HCID 17856978, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To 10.7 g of 3-benzyloxy-N-(5-bromo-2-pyridyl)-2-nitrobenzamide were added 50 ml of trifluoroacetic acid and 4.88 g of pentamethylbenzene and the mixture was stirred at room temperature for 4 days. The reaction solution was concentrated in vacuo, to the residue was added a saturated aqueous solution of sodium hydrogen carbonate to such an extent that the residue did not become alkaline and the mixture was extracted with chloroform. The organic layer was extracted with 1N aqueous solution of sodium hydroxide and concentrated hydrochloric acid was added to an aqueous layer. The resulting precipitate was collected by filtration and dried in vacuo to give 7.86 g of N-(5-bromo-2-pyridyl)-3-hydroxy-2-nitrobenzamide.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo, to the residue
  2. additionwas added a saturated aqueous solution of sodium hydrogen carbonate to such an extent that the residue
  3. extractionthe mixture was extracted with chloroform
  4. extractionThe organic layer was extracted with 1N aqueous solution of sodium hydroxide and concentrated hydrochloric acid
  5. additionwas added to an aqueous layer
  6. filtrationThe resulting precipitate was collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-65a38d3fa3914cd8a6e03e67d37dd0f5
Source dataset
uspto-grants-2009_03
Patent number
US07504417B2

Reaction notes

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