Diethyl Ether → HCID 11358577, compound

HRID 581906Notes

Reaction equation

HRID 581906 reaction equation
C([C:4]1[CH:5]=[CH:6][C:7]([N+:23]([O-])=O)=[C:8]([CH:22]=1)[NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:11]=1)(=O)C.[CH2:26]([O:28]CC)[CH3:27]>C(O)C.ClCCl.[Pd]>[C:26]([C:5]1[CH:4]=[CH:22][C:8]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[CH:11]=2)=[C:7]([CH:6]=1)[NH2:23])(=[O:28])[CH3:27]

Participants

6

Reactant 2

HCID 3283Diethyl EtherHCID 53753184HCID 53753184, compound

Product 1

HCID 11358577HCID 11358577, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

30a from Example 12 (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. Trituration with a mixture of diethyl ether and petroleum ether (1:1) affords 1.46 g pure 31a (80%). Mp 175-176° C.

Workup

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

Sources & evidence

ORD record
ord-db37038ef257476db9a62e653c3c33f7
Source dataset
uspto-grants-1999_07
Patent number
US05922725

Reaction notes

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