HCID 4780303, compound → HCID 11469830, compound

HRID 272512Notes

Reaction equation

HRID 272512 reaction equation
[CH3:1][CH:2]1[O:7][CH:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-])=O)=[CH:13][CH:14]=2)[CH2:3]1>C1COCC1.[Ni]>[CH3:1][CH:2]1[O:7][CH:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[N:11][CH:10]=2)[CH2:3]1

Participants

4

Reactant 1

HCID 4780303HCID 4780303, compound

Product 1

HCID 11469830HCID 11469830, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2,6-Dimethyl-4-(6-nitro-pyridin-3-yl)-morpholine (4.00 g, 16.86 mmol) was dissolved in THF (100 mL) to which Raney Nickel (3.10 g) was added. The reaction mixture was shaken under a hydrogen atmosphere (50 psi) for 4 hours. The catalyst was filtered and the solvent evaporated to give 5-(2,6-dimethyl-morpholin-4-yl)-pyridin-2-ylamine as a purple solid (3.05 g, 87.4%). 1H NMR δ(400 MHz, CDCl3) 7.74 (d, J=2.4 Hz, 1H), 7.16 (dd, J=2.9, 8.8 Hz, 1H), 6.49 (dd, J=0.7, 8.8 Hz, 1H), 3.79 (m, 2H), 2.34 (dd, J=10.5, 10.5, 2H), 1.22 (d, J=6.3 Hz, 6H).

Workup

  1. additionwas added
  2. filtrationThe catalyst was filtered
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-25b04ee652d34377a41145fae1140db4
Source dataset
uspto-grants-2008_11
Patent number
US07456168B2

Reaction notes

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