HCID 11026176, compound → HCID 11011989, compound

HRID 1870620Notes

Reaction equation

HRID 1870620 reaction equation
[N+:1]([C:4]1[C:26]([F:27])=[C:25]([F:28])[C:7]([O:8][C:9]2[CH:24]=[CH:23][C:12]([C:13]([O:15]CC3C=CC=CC=3)=[O:14])=[CH:11][CH:10]=2)=[C:6]([F:29])[C:5]=1[OH:30])([O-])=O.[H][H]>O1CCCC1.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[C:26]([F:27])=[C:25]([F:28])[C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:23][CH:24]=2)=[C:6]([F:29])[C:5]=1[OH:30]

Participants

6

Reactant 2

HCID 11026176HCID 11026176, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11011989HCID 11011989, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

50 g of benzyl 4-(4-nitro-3-hydroxy-2,5,6-trifluorophenoxy)benzoate prepared as described in Example 1 (0.12 mol) are dissolved in 600 ml of a mixture of tetrahydrofuran and ethyl acetate (volume ratio 1:1), and 5 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 and left to stand overnight at room temperature, during which the reaction product precipitates out 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 (yield: 93%).

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. waitleft
  6. waitto stand overnight at room temperature, during which
  7. customthe reaction product precipitates out 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 (yield: 93%)

Sources & evidence

ORD record
ord-13e5ac5909a0490ab027986966fb6bce
Source dataset
uspto-grants-2000_08
Patent number
US06096921

Reaction notes

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