Methyl 6-amino-5-nitropyridine-3-carboxylate → Methyl 5,6-diaminopyridine-3-carboxylate

HRID 854095Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([NH2:13])=[N:6][CH:5]=1>CO.[Ni]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH2:13])=[N:6][CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 6-Amino-5-nitro-nicotinic acid methyl ester (3) (5 g, 25 mmol) in MeOH (150 ml) was added Raney Ni. The mixture was vacuum purged with H2 5 times and heated at 80° C. under H2 atmosphere for 4 h. The solution was filtered through celite and concentrated in vacuo to give the product as a brown solid (3.2 g, 19 mmol, 76%) that was used without further purification. TLC of the product in DCM/MeOH (19:1) indicated a more polar spot at Rf=0.026.

Workup

custompurged with H2 5 times
filtrationThe solution was filtered through celite and
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-e13450cda6314389bd2b3de44eb0b45b
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07256287B2

Reaction notes

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