(2-Methoxy-ethyl)-(6-methyl-5-nitro-pyridin-2-yl)-amine → N2-(2-Methoxy-ethyl)-6-methyl-pyridine-2,5-diamine

HRID 1811557Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]([CH3:15])[N:7]=1>[Zn].C(O)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([CH3:15])[N:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of (2-methoxy-ethyl)-(6-methyl-5-nitro-pyridin-2-yl)-amine (421 mg, 2 mmol) and 5 ml of acetic acid, Zn dust (781 mg, 12 mmol) was added at 0° C. The mixture was stirred at 60° C. for 1 hour. Zn dust was filtered through celite and the residue was purified by HPLC to provide N2-(2-Methoxy-ethyl)-6-methyl-pyridine-2,5-diamine as an oil (140 mg, 39%). Exact mass calculated for C9H15N3O 181.12 found 182.2 (MH+).

Workup

additionwas added at 0° C
filtrationZn dust was filtered through celite
customthe residue was purified by HPLC

Sources & evidence

ORD record: ord-60ee3a2d84c144648e7615b5dcf9fd61
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362248B2

Reaction notes

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