HCID 54236417, compound → HCID 12900263, compound

HRID 1389690Notes

Reaction equation

HRID 1389690 reaction equation
[C:1]1([O:7][C:8]([C:10]2[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[C:12]([C:19]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:20])[C:11]=2[C:28]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:29])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CN(C)C=O.[Pd]>[C:1]1([O:7][C:8]([C:10]2[CH:15]=[C:14]([NH2:16])[CH:13]=[C:12]([C:19]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:20])[C:11]=2[C:28]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:29])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 54236417HCID 54236417, compound

Product 1

HCID 12900263HCID 12900263, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 29.0 g. of 5-nitro-1,2,3-benzenetricarboxylic acid triphenyl ester in dimethylformamide is hydrogenated on a Parr shaker in the presence of 10% palladium-on-carbon catalyst. The mixture is filtered through diatomaceous earth and the filtrate is diluted with water and extracted with methylene chloride. The extract is dried over anhydrous sodium sulfate and evaporated to give an oil. The oil is crystallized from ether, and the solid is recrystallized from benzene and twice from ethanol to provide 15.0 g of the product of the Example.

Workup

  1. filtrationThe mixture is filtered through diatomaceous earth
  2. additionthe filtrate is diluted with water
  3. extractionextracted with methylene chloride
  4. dry with materialThe extract is dried over anhydrous sodium sulfate
  5. customevaporated
  6. customto give an oil
  7. customThe oil is crystallized from ether
  8. customthe solid is recrystallized from benzene and twice from ethanol

Sources & evidence

ORD record
ord-d78cbbd09575453cb2c327b2b2683ed5
Source dataset
uspto-grants-1981_01
Patent number
US04245120

Reaction notes

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