Ammonium formate → HCID 68517527, compound

HRID 732784Notes

Reaction equation

HRID 732784 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=3)[C:12]=2[O:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C([O-])=O.[NH4+]>[OH-].[OH-].[Pd+2].C(O)C>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=3)[C:12]=2[O:23][C:24]2[CH:25]=[CH:26][C:27]([NH2:30])=[CH:28][CH:29]=2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 685194862-[4-(Methanesulfonyl)phenyl]-6-methoxy-1-(4-nitrophenoxy)naphthalene

Product 1

HCID 68517527HCID 68517527, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Heat a solution of 2-(4-methanesulfonyl-phenyl)-6-methoxy-1-(4-nitro-phenoxy)-naphthalene (1.67 g, 3.7 mmol), ammonium formate (4.7 g, 74 mmol), wet 20% palladium hydroxide on carbon (420 mg, 25 wt %) and absolute ethanol (80 mL) at reflux for 1 hour, then cool to ambient temperature, filter and evaporate to dryness under reduced pressure. Partition the residue with dichloromethane/water. Dry the organic layer with solid magnesium sulfate and chromatograph on silica gel with dichloromethane/methanol mixtures to give 1.15 g of 4-[2-(4-methanesulfonyl-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenylamine (75%).

Workup

  1. temperatureat reflux for 1 hour
  2. filtrationfilter
  3. customevaporate to dryness under reduced pressure
  4. customPartition the residue with dichloromethane/water
  5. dry with materialDry the organic layer with solid magnesium sulfate and chromatograph on silica gel with dichloromethane/methanol

Sources & evidence

ORD record
ord-9f473e52186240e0b939087b0238a484
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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