Ethanol → HCID 18174658, compound

HRID 395699Notes

Reaction equation

HRID 395699 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([N+:26]([O-])=O)[CH:22]=3)[C:17]2=[O:29])=[O:8])=[CH:5][CH:4]=1.C(O)C.[H][H]>[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:16]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([NH2:26])[CH:22]=3)[C:17]2=[O:29])=[O:8])=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 18174446HCID 18174446, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18174658HCID 18174658, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(4-methoxybenzoyl)-2-(5-nitro-1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)benzeneamine (1.11 g, 2.66 mmol) and 5% palladium-on-carbon (1.21 g) in 2:1 ethanol:ethyl acetate (200 mL) was placed under 1 atmosphere of hydrogen. After consumption of the starting material (about 2-3 h), the mixture was filtered through diatomaceous earth and the resulting filtrate concentrated in vacuo. Recrystallization from hexanes/ethyl acetate yielded 596 mg (58% of the title-compound.

Workup

  1. customAfter consumption of the starting material (about 2-3 h)
  2. filtrationthe mixture was filtered through diatomaceous earth
  3. concentrationthe resulting filtrate concentrated in vacuo
  4. customRecrystallization from hexanes/ethyl acetate

Sources & evidence

ORD record
ord-19cb10c6ee07469aa342adf58cab816d
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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