HCID 18433622, compound → HCID 18433566, compound

HRID 2306251Notes

Reaction equation

HRID 2306251 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([CH:18]=1)=[C:16]([N+:19]([O-])=O)[CH:15]=[CH:14][CH:13]=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CCO>[NH2:19][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1[CH:18]=[C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])[CH:10]=[N:11]2

Participants

3

Reactant 1

HCID 18433622HCID 18433622, compound

Product 1

HCID 18433566HCID 18433566, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(tert-Butyldimethylsilyloxy)-5-nitroquinoline, as described above in Step E, (4.58 g, 15.04 mmol) was dissolved in EtOH (150 mL) and EtOAc (150 mL), the vessel was degassed, Pd/C (0.458 g, 10 wt %) was added and the mixture was subjected to H2 (1 atm) with vigorous stirring for 1 hour. The mixture was filtered through a celite pad and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with a gradient of 0% to 10% EtOAc in CH2Cl2, to yield the above-titled compound.

Workup

  1. customEtOAc (150 mL), the vessel was degassed
  2. additionPd/C (0.458 g, 10 wt %) was added
  3. filtrationThe mixture was filtered through a celite pad
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel
  6. washeluting with a gradient of 0% to 10% EtOAc in CH2Cl2

Sources & evidence

ORD record
ord-0a867fc34bf94d41b629140b36e30aee
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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