2-Morpholino-5-nitropyridine → 6-(Morpholino)pyridin-3-amine

HRID 41521

Reaction equation

HRID 41521 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[N:8][CH:9]=1)([O-])=O>[Pd].CCO>[O:13]1[CH2:14][CH2:15][N:10]([C:7]2[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:11][CH2:12]1

Participants

4

Reactant 1

HCID 968722-Morpholino-5-nitropyridine

Product 1

HCID 1040596-(Morpholino)pyridin-3-amineYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Into a EtOH (250 mL) solution of 4-(5-nitropyridin-2-yl)morpholine (4.9 g, 23.4 mmol), 10% Pd on activated carbon, 500 mg, was added. Hydrogenation was carried out in a Parr flask at room temperature, at 40 psi for 2 hr. The solids were filtered off and the filtrate was collected. The solvent was removed in vacuo. 6-Morpholinopyridin-3-amine, as a purple solid, was obtained: 3.7 g (88% yield); 1H NMR (300 MHz, DMSO) δ 7.64 (d, J=2.7, 1H), 6.96 (dd, J=2.7, 8.8, 1H), 6.65 (d, J=8.8, 1H), 4.63 (s, 2H), 3.72-3.69 (m, 4H), 3.21-3.18 (m, 4H); LCMS (M+) m/z 180.08.

Workup

  1. filtrationThe solids were filtered off
  2. customthe filtrate was collected
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-15d4a256c20c4296b5d0ea57097fe0d3
Source dataset
uspto-grants-2013_09
Patent number
US08530656B2

Linked notes

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