Pentamethylbenzene → 2-amino-N-(5-chloro-2-pyridinyl)-3-hydroxybenzamide

HRID 506532Notes

Reaction equation

HRID 506532 reaction equation
C([O:8][C:9]1[C:10]([N+:25]([O-])=O)=[C:11]([CH:22]=[CH:23][CH:24]=1)[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl: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>[NH2:25][C:10]1[C:9]([OH:8])=[CH:24][CH:23]=[CH:22][C:11]=1[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=1)=[O:13]

Participants

4

Reactant 2

HCID 12784PentamethylbenzeneHCID 180011353-benzyloxy-N-(5-chloro-2-pyridyl)-2-nitrobenzamide

Product 1

HCID 180011272-amino-N-(5-chloro-2-pyridinyl)-3-hydroxybenzamideYield 89.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
40 °C

Procedure

To 7.44 g of 3-benzyloxy-N-(5-chloro-2-pyridyl)-2-nitrobenzamide were added 40 ml of trifluoroacetic acid and 3.72 g of pentamethylbenzene and the mixture was stirred at 40° C. for one night. 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, the aqueous layer was made acidic by addition of hydrochloric acid thereto and the mixture was extracted with chloroform. The extract was dried over anhydrous magnesium sulfate, the solvent was evaporated in vacuo and to the resulting residue were added 200 ml of suspension of Raney nickel in ethanol. This was stirred for 6 hours in a hydrogen atmosphere, N,N-dimethylformamide was added thereto and the insoluble matter was filtered off. The solvent was evaporated in vacuo and water was added to the resulting residue. The resulting precipitate was collected by filtration and dried in vacuo to give 4.58 g of 2-amino-N-(5-chloro-2-pyridyl)-3-hydroxybenzamide.

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
  5. additionthe aqueous layer was made acidic by addition of hydrochloric acid
  6. extractionthe mixture was extracted with chloroform
  7. dry with materialThe extract was dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated in vacuo and to the resulting residue
  9. additionwere added 200 ml of suspension of Raney nickel in ethanol
  10. stirringThis was stirred for 6 hours in a hydrogen atmosphere, N,N-dimethylformamide
  11. additionwas added
  12. filtrationthe insoluble matter was filtered off
  13. customThe solvent was evaporated in vacuo and water
  14. additionwas added to the resulting residue
  15. filtrationThe resulting precipitate was collected by filtration
  16. customdried in vacuo

Sources & evidence

ORD record
ord-fb186b35b2354534a8e062722c5653a4
Source dataset
uspto-grants-2010_08
Patent number
US07786106B2

Reaction notes

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