4-(4-Nitro-3-trifluoromethylphenoxy)pyridin-2-ylamine → 4-(4-Amino-3-trifluoromethylphenoxy)pyridin-2-ylamine

HRID 492710Notes

Reaction equation

HRID 492710 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=2)=[CH:6][C:5]=1[C:18]([F:21])([F:20])[F:19])([O-])=O>CO.[C].[Pd]>[NH2:1][C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=2)=[CH:6][C:5]=1[C:18]([F:21])([F:19])[F:20]

Participants

4

Reactant 1

HCID 231531074-(4-Nitro-3-trifluoromethylphenoxy)pyridin-2-ylamine

Product 1

HCID 231530904-(4-Amino-3-trifluoromethylphenoxy)pyridin-2-ylamineYield 55.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(4-nitro-3-trifluoromethylphenoxy)pyridin-2-ylamin (400 mg, 1.34 mmol) in methanol (20 ml) was added 10% palladium carbon (146 mg), followed by stirring under a hydrogen atmosphere at room temperature for 10 hrs. The reaction mixture was filtered to remove the catalyst. The filtrate was concentrated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (eluent; ethyl acetate) to provide the titled compound (201 mg, 55.4%) as a brown oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated under a reduced pressure
  4. customto give a residue, which
  5. customwas then purified by silica gel column chromatography (eluent; ethyl acetate)

Sources & evidence

ORD record
ord-19e20deaf37c49bf8605a3ef9f341f4b
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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