Diethyl Ether → HCID 11358577, compound

HRID 581974Notes

Reaction equation

HRID 581974 reaction equation
[C:1]([C:4]1[CH:22]=[CH:21][C:7]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH:10]=2)=[C:6]([N+:23]([O-])=O)[CH:5]=1)(=[O:3])[CH3:2].C(OCC)C>C(O)C.ClCCl.[Pd]>[C:1]([C:4]1[CH:22]=[CH:21][C:7]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH:10]=2)=[C:6]([CH:5]=1)[NH2:23])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 3283Diethyl EtherHCID 11325073HCID 11325073, compound

Product 1

HCID 11358577HCID 11358577, compoundYield 80.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

4-acetyl-2-nitro-N-(3-(3-pyridyl)-phenyl)-aniline (2 g, 6 mmol) is suspended in a mixture of ethanol (50 ml) and dichloromethane (10 ml) and is hydrogenated at ambient pressure using palladium (5% on activated carbon) as the catalyst. Filtration of the resulting solution through celite followed by evaporation of solvent leaves an oil which upon trituration with a mixture of diethylether and petroleumether (1:1) affords 1.46 g pure 5-acetyl-2-(3-(3-pyridyl)phenylamino)aniline (80%).

Workup

  1. filtrationFiltration of the resulting solution through celite
  2. customfollowed by evaporation of solvent
  3. customleaves an oil which upon trituration

Sources & evidence

ORD record
ord-e63a214c800d4a1ba379cdada0eaf0bc
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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