Methanol → 6-(6,7-Dimethoxyquinolin-4-yloxy)pyridin-3-amine

HRID 455807Notes

Reaction equation

HRID 455807 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][N:17]=1.C1COCC1.CO>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[N:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 229362516,7-Dimethoxy-4-(5-nitro-pyridin-2-yloxy)-quinoline2×

Product 1

HCID 229365976-(6,7-Dimethoxyquinolin-4-yloxy)pyridin-3-amineYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a round bottom flask equipped with a magnetic stir bar was added 6,7-dimethoxy-4-(5-nitro-pyridin-2-yloxy)-quinoline (0.46 g, 1.41 mmol, 1.0 eq.), and THF (10 mL), MeOH (4 mL), DMF (2 mL), and TEA (2 mL). The 6,7-Dimethoxy-4-(5-nitro-pyridin-2-yloxy)-quinoline was dissolved completely in the above solution mixture, and was flushed with nitrogen for at least 5 minutes. The Pd/C (10% by weight) (0.090 g, 20% by weight) was then added. A balloon filled with H2 was connected to the flask after the nitrogen was vacuumed out. The reaction mixture was stirred at room temperature for 4 hours. The palladium was filtered out through Celite, and the filtrated was collected and concentrated via rotary evaporation. The resulting oil-like product was taken up into 5 mL of water and 1 mL of acetonitrile and lyophilized to yield 6-(6,7-dimethoxy-quinolin-4-yloxy)-pyridin-3-ylamine as a light brown solid (0.411 g, 98.1%). 1H NMR (400 MHz, CDCl3): 8.54 (d, 1H), 7.85 (d, 1H), 7.53 (s, 1H), 7.41 (s, 1H), 7.18 (dd, 1H), 6.96 (d, 1H), 6.61 (d; 1H), 4.05 (s, 3H), 4.03 (s, 3H), 3.73 (s, 2H); MS (EI) for C16H15N3O3: 298 (M+H+).

Workup

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. customwas flushed with nitrogen for at least 5 minutes
  3. additionThe Pd/C (10% by weight) (0.090 g, 20% by weight) was then added
  4. additionA balloon filled with H2
  5. filtrationThe palladium was filtered out through Celite
  6. customthe filtrated was collected
  7. concentrationconcentrated via rotary evaporation

Sources & evidence

ORD record
ord-b3260d5eb60349bf85dd16fc9fbfdec9
Source dataset
uspto-grants-2013_07
Patent number
US08497284B2

Reaction notes

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