(3-Nitro-5-chloro-pyridin-2-yl)-(2,4-dimethyl-pyridin-3-yl)-methanone → (3-Amino-5-chloro-pyridin-2-yl)-(2,4-dimethyl-pyridin-3-yl)-methanone

HRID 1438544Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of iron powder (220 mg, 4.0 mmol) in 4 ml of acetic acid at 80° C. was slowly added a solution of (3-Nitro-5-chloro-pyridin-2-yl)-(2,4-dimethyl-pyridin-3-yl)-methanone (260 mg, 0.89 mmol) in 2 ml of acetic acid. After the completion of addition the mixture was stirred at 80° C. for half an hour and then cooled. The mixture was diluted with ethyl acetate, filtered through celite and the filtrate was concentrated. The residue was purified by flash column (50% ethyl acetate in hexane) to afford 140 mg of title compound as off-white solid. MS: (M+H)/z =262.0.

Workup

additionAfter the completion of addition the mixture
temperaturecooled
filtrationfiltered through celite
concentrationthe filtrate was concentrated
customThe residue was purified by flash column (50% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-fbfbb15aa3f946da9273ed759012ea5c
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622583B2

Reaction notes

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