HCID 86689777, compound → HCID 86689778, compound

HRID 1396434Notes

Reaction equation

HRID 1396434 reaction equation
[CH2:1]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[C:6]([N+:12]([O-])=O)[N:5]=1)[CH:2]=[CH2:3]>C(O)C.[Pd]>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][C:6]([NH2:12])=[N:5][C:4]=1[CH2:1][CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 86689777HCID 86689777, compound

Product 1

HCID 86689778HCID 86689778, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-allyl-3-methoxy-6-nitropyridine (2.0 g, 10.3 mmol) in ethanol (34 mL) was added 10% palladium on carbon (219 mg, 2.06 mmol). The reaction was evacuated and back filled with hydrogen. This was repeated two more times. The reaction mixture was stirred under hydrogen at 1 atm for 16 h, then filtered through a pad of celite and the filter cake washed thoroughly with ethyl acetate. The filtrates were concentrated in vacuo and purified by chromatography (silica, 25 to 90% ethyl acetate in hexanes) to give 5-methoxy-6-propylpyridin-2-amine (1.41 g, 8.48 mmol, 82%) as an off white solid. 1H NMR (400 MHz, CHLOROFORM-d6) δ ppm 7.09 (d, J=8.8 Hz, 1H), 6.38 (d, J=8.8 Hz, 1H), 4.28 (br. s, 2H), 3.77 (s, 3H), 2.68 (t, J=7.9 Hz, 2H), 1.69 (m, 2H), 0.99 (t, J=7.4 Hz, 3H); MS (EI/CI) m/z: 166.8 [M+H].

Workup

  1. customThe reaction was evacuated
  2. additionback filled with hydrogen
  3. filtrationfiltered through a pad of celite
  4. washthe filter cake washed thoroughly with ethyl acetate
  5. concentrationThe filtrates were concentrated in vacuo
  6. custompurified by chromatography (silica, 25 to 90% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f787de78c6bc4f99baf6d478be60e2d4
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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