[4-Nitro-2-(2,2,2-trifluoroethoxy)phenyl](pyridin-2-yl)methanol → HCID 69522388, compound

HRID 856616Notes

Reaction equation

HRID 856616 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[OH:11])=[C:6]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])[CH:5]=1)([O-])=O>C(O)C.[C].[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[OH:11])=[C:6]([O:18][CH2:19][C:20]([F:23])([F:21])[F:22])[CH:5]=1

Participants

4

Reactant 1

HCID 69522155[4-Nitro-2-(2,2,2-trifluoroethoxy)phenyl](pyridin-2-yl)methanol

Product 1

HCID 69522388HCID 69522388, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

[4-nitro-2-(2,2,2-trifluoroethoxy)phenyl](pyridin-2-yl)methanol (4.5 g) was dissolved in ethanol (150 ml), and the solution was reduced by catalytic hydrogenation overnight with 10% palladium-carbon of 50% hydration (0.25 g). The catalyst was removed, and the solvent of the filtrate was distilled off. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate), to give [4-amino-2-(2,2,2-trifluoroethoxy)phenyl](pyridin-2-yl)methanol (3.6 g) as yellow crystals.

Workup

  1. customThe catalyst was removed
  2. distillationthe solvent of the filtrate was distilled off
  3. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate)

Sources & evidence

ORD record
ord-3b5f827446824ab4a882b1388e75abc1
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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