4-(4-Nitro-3-benzyloxyphenoxy)-2-(4-benzyloxycarbonylphenoxy)-3,5,6-trifluoropyridine → 4-(4-Amino-3-hydroxyphenoxy)-2-(4-carboxyphenoxy)-3,5,6-trifluoropyridine

HRID 2305001Notes

Reaction equation

HRID 2305001 reaction equation
[N+:1]([C:4]1[CH:36]=[CH:35][C:7]([O:8][C:9]2[C:14]([F:15])=[C:13]([F:16])[N:12]=[C:11]([O:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([O:26]CC4C=CC=CC=4)=[O:25])=[CH:20][CH:19]=3)[C:10]=2[F:34])=[CH:6][C:5]=1[O:37]CC1C=CC=CC=1)([O-])=O.[H][H]>O1CCCC1.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:36]=[CH:35][C:7]([O:8][C:9]2[C:14]([F:15])=[C:13]([F:16])[N:12]=[C:11]([O:17][C:18]3[CH:19]=[CH:20][C:21]([C:24]([OH:26])=[O:25])=[CH:22][CH:23]=3)[C:10]=2[F:34])=[CH:6][C:5]=1[OH:37]

Participants

6

Reactant 2

HCID 184593394-(4-Nitro-3-benzyloxyphenoxy)-2-(4-benzyloxycarbonylphenoxy)-3,5,6-trifluoropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 177867214-(4-Amino-3-hydroxyphenoxy)-2-(4-carboxyphenoxy)-3,5,6-trifluoropyridineYield 91%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

40 g of the 4-(4-nitro-3-benzyloxyphenoxy)-2-(4-benzyloxycarbonylphenoxy)-3,5,6-trifluoropyridine prepared as described in Example 7 (0.066 mol) are dissolved in 600 ml of a mixture of tetrahydrofuran and ethyl acetate (volume ratio 1:1), and 4 g of Pd/C (palladium/carbon) are added to the solution. The mixture is then hydrogenated using hydrogen at a pressure of 1 bar at room temperature in an autoclave with vigorous stirring; the reaction is terminated after 3 days. The orange solution is evaporated to half in a rotary evaporator and left to stand overnight at room temperature, during which the reaction product precipitates out in crystalline form. The reaction product is then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet (yield: 91%).

Workup

  1. additionare added to the solution
  2. customat room temperature
  3. customthe reaction is terminated after 3 days
  4. customThe orange solution is evaporated to half in a rotary evaporator
  5. waitleft
  6. customthe reaction product precipitates out in crystalline form
  7. customThe reaction product is then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  8. customdrying cabinet (yield: 91%)

Sources & evidence

ORD record
ord-2b2d33c968d444cf962cd1a8bf0581c3
Source dataset
uspto-grants-2002_08
Patent number
US06437178B2

Reaction notes

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