2-(1,3-Dioxolan-2-yl)-3-nitropyridine → 2-(1,3-Dioxolanyl)-3-aminopyridine

HRID 473404Notes

Reaction equation

HRID 473404 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][N:7]=1>C(O)C.[Pd]>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 1

HCID 3293622-(1,3-Dioxolan-2-yl)-3-nitropyridine

Product 1

HCID 3293632-(1,3-Dioxolanyl)-3-aminopyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(1,3-Dioxolan-2-yl)-3-nitropyridine (10 g, 51 mmol) was suspended in ethanol (300 mL). To the mixture was added 10% Pd/C (3 g). The reaction mixture was kept at 60 psi pressure using Parr-shaker hydrogenation assembly. After completion of reaction (6 h), the reaction mixture was filtered through Celite™ and the filtrate was concentrated under reduced pressure to give 2-(1,3-dioxolan-2-yl)-3-pyridinamine as an off orange solid: 1H-NMR (CDCl3) δ: 4.4-4.0 (m, 6H), 5.8 (s, 1H), 7.2-6.9 (m, 2H), 8.0 (s, 1H).

Workup

  1. customAfter completion of reaction (6 h)
  2. filtrationthe reaction mixture was filtered through Celite™
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-778566ff162e40edae60b03cebeebc31
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Reaction notes

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