HCID 86675896, compound → HCID 178432269, compound

HRID 1619451Notes

Reaction equation

HRID 1619451 reaction equation
[C:1]([N:4]([C:8]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][C:11]([N+:18]([O-])=O)=[CH:10][C:9]=1[N+:21]([O-])=O)C(=O)C)(=O)[CH3:2].[H][H]>C(O)(=O)C.[Pd]>[CH3:2][C:1]1[NH:4][C:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][C:11]([NH2:18])=[CH:10][C:9]=2[N:21]=1

Participants

5

Reactant 2

HCID 86675896HCID 86675896, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178432269HCID 178432269, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 0.63 g I.11 (N-acetyl-N-(2,4-dinitro-6-trifluoromethyl-phenyl)-acetamide) and 0.2 g Pd/C 10% in 20 ml glacial acetic acid was stirred for 5 h at 80° C. under a pressure of hydrogen of 50 psi. The catalyst was filtered and the solvent was evaporated. To the residue, 30 ml glacial acetic acid were added and the mixture was stirred for 2 h at reflux. The solvent was removed. The residue was treated with 50 ml 4 N aqueous hydrochloric acid and stirred for 1 h at reflux. The reaction mixture was cooled down to ambient temperature and the pH was adjusted to ˜7 with potassium carbonate. The resulting precipitate was filtered, washed with 30 ml water and dried.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent was evaporated
  3. additionTo the residue, 30 ml glacial acetic acid were added
  4. temperatureat reflux
  5. customThe solvent was removed
  6. additionThe residue was treated with 50 ml 4 N aqueous hydrochloric acid
  7. stirringstirred for 1 h
  8. temperatureat reflux
  9. filtrationThe resulting precipitate was filtered
  10. washwashed with 30 ml water
  11. customdried

Sources & evidence

ORD record
ord-8f3dc544656f4e95b2faa3db44f2086d
Source dataset
uspto-grants-2014_07
Patent number
US08772305B2

Reaction notes

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