HCID 86689782, compound → HCID 86689783, compound

HRID 1396440Notes

Reaction equation

HRID 1396440 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:12]([CH3:14])=[CH2:13])=[N:5][C:6]([N+:9]([O-])=O)=[CH:7][CH:8]=1>C(O)C.[Pd]>[CH:12]([C:4]1[N:5]=[C:6]([NH2:9])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])([CH3:14])[CH3:13]

Participants

4

Reactant 1

HCID 86689782HCID 86689782, compound

Product 1

HCID 86689783HCID 86689783, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-methoxy-6-nitro-2-(prop-1-en-2-yl)pyridine (824 mg, 4.24 mmol) in ethanol (14.1 mL) was added 10% palladium on carbon (45.2 mg, 424 μmol). The reaction mixture was evacuated and back filled with hydrogen. This was repeated two more times. The reaction was stirred under hydrogen at 1 atm for 16 h. The mixture was then filtered reaction through a pad of celite, the filtrate concentrated in vacuo, and then purified by chromatography (silica, 10 to 60% ethyl acetate in hexanes) to give 6-isopropyl-5-methoxypyridin-2-amine (562 mg, 3.38 mmol, 80%) as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d6) δ ppm 7.04 (d, J=8.7 Hz, 1H), 6.33 (d, J=8.7 Hz, 1H), 4.12 (br. s, 2H), 3.78 (s, 3H), 3.36 (m, 1H), 1.22 (d, J=7.0 Hz, 6H); MS (EI/CI) m/z: 166.8 [M+H].

Workup

  1. customThe reaction mixture was evacuated
  2. additionback filled with hydrogen
  3. filtrationThe mixture was then filtered
  4. customreaction through a pad of celite
  5. concentrationthe filtrate concentrated in vacuo
  6. custompurified by chromatography (silica, 10 to 60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7773f95f93d54a27a157e1a31aa30d36
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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