Ethanol → HCID 22236953, compound

HRID 1743978Notes

Reaction equation

HRID 1743978 reaction equation
[CH3:1][C:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)([CH2:9][N+:10]([O-])=O)[CH2:3][C:4](OCC)=O.C1(C)C=CC=CC=1.C([OH:28])C>[Ni]>[CH3:1][C:2]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C:3](=[O:28])[CH2:4][NH:10][CH2:9]1

Participants

5

Reactant 3

HCID 702EthanolHCID 1140TolueneHCID 22236902HCID 22236902, compound

Product 1

HCID 22236953HCID 22236953, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

A solution of 5.9 g of the compound obtained in Step 2 in 150 ml of ethanol was hydrogenated for 12 hours in the presence of 0.6 g of Raney nickel (10% w/w) under a hydrogen gas pressure of 60 psi. After the reaction was completed, the reaction solution was filtered with Celite® 545 and the filtrate was concentrated under reduced pressure. To the residue thus obtained was added 150 ml of toluene, and the resulting mixture was heated to reflux for 2 hours. The reaction product solution was concentrated under reduced pressure, and the residue thus obtained was purified by a silica gel column chromatography using a mixture of ethyl acetate and methanol of 9:1 to obtain 3.35 g of the title compound as a white solid.

Workup

  1. filtrationthe reaction solution was filtered with Celite® 545
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customTo the residue thus obtained
  4. temperaturethe resulting mixture was heated
  5. temperatureto reflux for 2 hours
  6. concentrationThe reaction product solution was concentrated under reduced pressure
  7. customthe residue thus obtained
  8. customwas purified by a silica gel column chromatography
  9. additiona mixture of ethyl acetate and methanol of 9:1

Sources & evidence

ORD record
ord-8434755b0fb946d39b769ac868c20915
Source dataset
uspto-grants-2006_03
Patent number
US07012144B2

Reaction notes

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