6-(1-Benzyl-pyrrolidin-3-yloxy)-2-methoxy-3-nitro-pyridine → 6-(1-Benzyl-pyrrolidin-3-yloxy)-2-methoxy-pyridin-3-ylamine

HRID 390291Notes

Reaction equation

[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[N:19]=[C:18]([O:20][CH3:21])[C:17]([N+:22]([O-])=O)=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.[Fe]>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[N:19]=[C:18]([O:20][CH3:21])[C:17]([NH2:22])=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-(1-benzyl-pyrrolidin-3-yloxy)-2-methoxy-3-nitro-pyridine (0.38 g, 1.15 mmol) in acetic acid (4 ml) at 80° C. was added iron (0.32 g, 5.77 mmol) slowly in portions. The exothermic reaction was stirred for 3 h at 80° C. After evaporation of the solvent under reduced pressure the solid residue was dissolved in 1N NaOH, which was extracted 6 times with dichloromethane. The combined organic layers were dried over MgSO4, filtered and the solvent evaporated to obtain 240 mg (68.9%) of the title compound.

Workup

customThe exothermic reaction
customAfter evaporation of the solvent under reduced pressure the solid residue
dissolutionwas dissolved in 1N NaOH
extractionwhich was extracted 6 times with dichloromethane
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
customthe solvent evaporated

Sources & evidence

ORD record: ord-681f9e13a6ec43f39a66219a3d6c523d
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383641B2

Reaction notes

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