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

HRID 1866044Notes

Reaction equation

HRID 1866044 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.[OH-].[Na+]>C(O)(=O)C.C(Cl)Cl.C([O-])(O)=O.[Na+].[Pt]=O>[NH2:1][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[NH:12][CH2:11][CH2:10][CH2:9]2

Participants

7

Reactant 2

HCID 118308-NitroquinolineHCID 14798Sodium Hydroxide

Product 1

HCID 1046728-Quinolinamine, 1,2,3,4-tetrahydro-Yield 79.4%

Reagents, catalysts & solvents 4

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 8-nitroquinoline (1.035 g, 5,94 mmol) and platinum oxide (35 mg, 0.15 mmol, 2.5 mol %) in glacial acetic acid was hydrogenated (20 psi) on a Parr Shaker at room temperature for 20 hours. The mixture was filtered through celite and the cake was washed with methanol. The solvent was removed from the filtrate to afford a red oil. The oil was dissolved in a mixture of CH2Cl2 (25 mL) and saturated aqueous NaHCO3 (10 mL) and a 10 M aqueous solution of sodium hydroxide was added dropwise until the aqueous phase was basic (pH ˜14) to litmus paper. The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were washed once with water (10 mL), dried (Na2SO4), and concentrated. The residue was filtered (100:1 CH2Cl2-CH3OH) through a short pad of silica gel (30 g) and afforded 0.699 g (79%) of 8-amino-1,2,3,4-tetrahydroquinoline as an oil. 1H NMR (CDCl3) δ 1.89-1.97 (m, 2H), 2.79 (t, 2H, J=6.3 Hz), 3.34 (t, 2H, J=5.4 Hz), 3.20-3.60 (br signal, 3H, NH & NH2), 6.55-6.64 (m, 3H); 13C NMR (CDCl3) δ 22.79, 27.44, 42.98, 114.50, 118.47, 121.56, 123.70, 134.24 (2 carbons).

Workup

  1. customat room temperature
  2. customfor 20 hours
  3. filtrationThe mixture was filtered through celite
  4. washthe cake was washed with methanol
  5. customThe solvent was removed from the filtrate
  6. customto afford a red oil
  7. customThe phases were separated
  8. extractionthe aqueous phase was extracted with CH2Cl2 (3×10 mL)
  9. washThe combined organic extracts were washed once with water (10 mL)
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated
  12. filtrationThe residue was filtered (100:1 CH2Cl2-CH3OH) through a short pad of silica gel (30 g)

Sources & evidence

ORD record
ord-f599a188ff9b4f658096cdcfa6c87d4f
Source dataset
uspto-grants-2009_12
Patent number
US07629337B2

Reaction notes

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