8-Nitroquinoline → 8-Quinolinamine, 1,2,3,4-tetrahydro-

HRID 2374599Notes

Reaction equation

HRID 2374599 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-])=O.[H][H]>[Pt]=O.C(O)(=O)C>[NH:12]1[C:13]2[C:8](=[CH:7][CH:6]=[CH:5][C:4]=2[NH2:1])[CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 118308-NitroquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 1046728-Quinolinamine, 1,2,3,4-tetrahydro-Yield 71.4%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A mixed solution of 8-nitroquinoline (25.0 g), platinum oxide (600 mg) and glacial acetic acid (300 ml) was stirred at room temperature for 4 hours under the atmosphere of hydrogen at 5 atm. The reaction mixture was filtered through Celite, and the solvent was evaporated under reduced pressure. Then, the solution was extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and purified by silica gel column chromatography to give the title compound as a reddish brown oil (15.2 g).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was evaporated under reduced pressure
  3. extractionThen, the solution was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-d54f9316f9e5408999bafb7b36b5de55
Source dataset
uspto-grants-2008_12
Patent number
US07462628B2

Reaction notes

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