HCID 21918590, compound → HCID 21918572, compound

HRID 2373743Notes

Reaction equation

HRID 2373743 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:21]=[C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:23]=1[OH:24])[C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=1)=[O:9])([CH3:4])[CH3:3].[H][H]>C(O)C.C1COCC1.[Pd]>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([CH:21]=[C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:23]=1[OH:24])[C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH2:18])[CH:13]=1)=[O:9])([CH3:1])[CH3:3]

Participants

5

Reactant 2

HCID 21918590HCID 21918590, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21918572HCID 21918572, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 23938PalladiumSolventHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

In a 250 ml Parr flask, 2.40 g (6.2 mmoles) of 3,5-bis-(1,1-dimethylethyl)-4-hydroxy-N-[(3-nitrophenyl)methyl]-benzamide is dissolved in 45 ml of an absolute ethanol/THF mixture (1/2) in the presence of 10% Pd/C. The mixture is agitated under 20 PSI of hydrogen, at 30° C., for three hours. After filtration on celite, the filtrate is concentrated to dryness and the residue is purified on a silica column (eluant: heptane/ethyl acetate: 60/40). The pure fractions are collected and concentrated under reduced pressure to produce 0.94 g (45%) of a white powder. Melting point: 171-172° C.

Workup

  1. filtrationAfter filtration on celite
  2. concentrationthe filtrate is concentrated to dryness
  3. customthe residue is purified on a silica column (eluant: heptane/ethyl acetate: 60/40)
  4. customThe pure fractions are collected
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-54d56c26c5644763a9665ae4a0502160
Source dataset
uspto-grants-2008_12
Patent number
US07459558B2

Reaction notes

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