2-Isopropoxy-5-nitropyridine → 6-(1-Methylethoxy)-3-pyridinamine

HRID 657233Notes

Reaction equation

HRID 657233 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][N:6]=1)([CH3:3])[CH3:2]>CO.[Pd]>[CH:1]([O:4][C:5]1[N:6]=[CH:7][C:8]([NH2:11])=[CH:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 120361742-Isopropoxy-5-nitropyridine

Product 1

HCID 214841416-(1-Methylethoxy)-3-pyridinamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-isopropoxy-5-nitro-pyridine, as prepared in the previous step, in MeOH (5 mL) was added 20 mg of 10% Pd/C. The mixture was degassed several times and stirred under hydrogen atmosphere for 4 h. It was filtered through a pad of celite and the filtrate was evaporated. The residue was purified by flash column chromatography on silica gel (EtOAc as eluent). 1H NMR (400 MHz, CDCl3) δ 7.65 (d, J=2.96 Hz, 1H), 7.02 (dd, J=8.71 and 2.99 Hz, 1H), 6.54 (d, J=8.67 Hz, 1H), 5.14 (m, 1H), 1.31 (d, J=6.17 Hz, 6H). LC-MS (ESI) calcd mass 152.1, found 153.2 (MH+).

Workup

  1. customThe mixture was degassed several times
  2. filtrationIt was filtered through a pad of celite
  3. customthe filtrate was evaporated
  4. customThe residue was purified by flash column chromatography on silica gel (EtOAc as eluent)

Sources & evidence

ORD record
ord-33bfb5fb5df847f3bca9ce0e82b13129
Source dataset
uspto-grants-2011_12
Patent number
US08071768B2

Reaction notes

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