HCID 22121150, compound → HCID 22121146, compound

HRID 1274518Notes

Reaction equation

HRID 1274518 reaction equation
[N+:1]([C:4]1[CH:37]=[CH:36][C:7]([O:8][C:9]2[C:14]([F:15])=[C:13]([O:16][C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[C:19]([O:26]CC4C=CC=CC=4)[CH:18]=3)[C:12]([F:34])=[C:11]([F:35])[N:10]=2)=[CH:6][C:5]=1[O:38]CC1C=CC=CC=1)([O-])=O.[H][H]>O1CCCC1.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:37]=[CH:36][C:7]([O:8][C:9]2[C:14]([F:15])=[C:13]([O:16][C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[C:19]([OH:26])[CH:18]=3)[C:12]([F:34])=[C:11]([F:35])[N:10]=2)=[CH:6][C:5]=1[OH:38]

Participants

6

Reactant 2

HCID 22121150HCID 22121150, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22121146HCID 22121146, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

99 g of 2,4-bis(4-nitro-3-benzyloxyphenoxy)-3,5,6-trifluoropyridine prepared as described in Example 5 (0.16 mol) are dissolved in 600 ml of a mixture of tetrahydrofuran and ethyl acetate (volume ratio 1:1), and 10 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-beige solution is evaporated to half in a rotary evaporator and left to stand overnight at room temperature, during which the reaction product precipitates in crystalline form. The reaction product is then collected 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-beige 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 in crystalline form
  8. customThe reaction product is then collected
  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-947982fc6ae74e7fb53c9c25f9c22354
Source dataset
uspto-grants-2000_12
Patent number
US06156902

Reaction notes

Loading…