1-(3-Hydroxy-4-nitro-2,5,6-trifluorophenoxy)-3-benzyloxy-4-nitrobenzene → 3-(3-Hydroxy-4-amino-2,5,6-trifluorophenoxy)-6-aminophenol

HRID 430057Notes

Reaction equation

HRID 430057 reaction equation
[OH:1][C:2]1[C:3]([F:31])=[C:4]([C:23]([F:30])=[C:24]([F:29])[C:25]=1[N+:26]([O-])=O)[O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]([O:15]CC2C=CC=CC=2)[CH:7]=1.[H][H]>O1CCCC1.C(OCC)(=O)C.[Pd]>[OH:1][C:2]1[C:3]([F:31])=[C:4]([C:23]([F:30])=[C:24]([F:29])[C:25]=1[NH2:26])[O:5][C:6]1[CH:7]=[C:8]([OH:15])[C:9]([NH2:12])=[CH:10][CH:11]=1

Participants

6

Reactant 2

HCID 183538411-(3-Hydroxy-4-nitro-2,5,6-trifluorophenoxy)-3-benzyloxy-4-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 183538363-(3-Hydroxy-4-amino-2,5,6-trifluorophenoxy)-6-aminophenol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

43.6 g of 1-(3-hydroxy-4-nitro-2,5,6-trifluorophenoxy)-3-benzyloxy-4-nitrobenzene prepared as described in Example 13 (0.1 mol) are dissolved in 400 ml of a mixture of tetrahydrofuran and ethyl acetate (volume ratio 1:1), and 4.4 g of Pd/C (palladium/carbon) are added to the solution. The mixture is then hydrogenated at room temperature in an autoclave with vigorous stirring using hydrogen at a pressure of 1 bar; after 3 days, the reaction is terminated. The yellow solution is evaporated to half in a rotary evaporator an left to stand at room temperature overnight, during which the reaction product precipitates in crystalline form. The reaction product is then separated off and dried for 48 hours under nitrogen at, 40° C./10 mbar in a vacuum drying cabinet.

Workup

  1. additionare added to the solution
  2. customis then hydrogenated at room temperature in an autoclave
  3. customthe reaction is terminated
  4. customThe yellow solution is evaporated to half in a rotary evaporator
  5. waitan left
  6. waitto stand at room temperature overnight, during which
  7. customthe reaction product precipitates in crystalline form
  8. customThe reaction product is then separated off
  9. customdried for 48 hours under nitrogen at, 40° C./10 mbar in a vacuum
  10. customdrying cabinet

Sources & evidence

ORD record
ord-f31172241dc04831885b7123486b289f
Source dataset
uspto-grants-2001_11
Patent number
US06320081B1

Reaction notes

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