HCID 14817945, compound → HCID 59773373, compound

HRID 2114291Notes

Reaction equation

HRID 2114291 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:11](=[O:13])[CH3:12])=[CH:4][C:3]=1[N+:14]([O-])=O>C(O)C.C(O)(=O)C.[Pd]>[NH2:14][C:3]1[CH:4]=[C:5]([CH2:8][CH2:9][O:10][C:11](=[O:13])[CH3:12])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

5

Reactant 1

HCID 14817945HCID 14817945, compound

Product 1

HCID 59773373HCID 59773373, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Aryl nitrate 187 was dissolved in neat ethanol (25 mL) and 10% Pd/C (50 mg) was added, followed by 3 drops of glacial acetic acid. H2 gas was applied at 46 psi for 2 h with vigorous shaking, after which time TLC analysis indicated complete consumption of 187. The reaction mixture was filtered through a pad of Celite to remove the catalyst and the filtrate was concentrated under reduced pressure to give 188 as an oil. Column chromatography was employed with 10% MeOH/CH2Cl2 as eluant to give pure 188 as a white solid.

Workup

  1. customconsumption of 187
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. customto remove the catalyst
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-38315b62789f4337b420a3da8a91787f
Source dataset
uspto-grants-2008_10
Patent number
US07432379B2

Reaction notes

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