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5-Nitro-3-(trifluoromethyl)-2-pyridinecarbonitrile → 5-Amino-3-(trifluoromethyl)pyridine-2-carbonitrile

HRID 1257087
Notes
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Reaction equation

HRID 1257087 reaction equation
[C:1]([C:3]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][C:6]([N+:13]([O-])=O)=[CH:5][N:4]=1)#[N:2]>CCOC(C)=O.CC(O)=O.[Fe]>[NH2:13][C:6]1[CH:7]=[C:8]([C:9]([F:12])([F:10])[F:11])[C:3]([C:1]#[N:2])=[N:4][CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 218748935-Nitro-3-(trifluoromethyl)-2-pyridinecarbonitrile

Product 1

HCID 135322465-Amino-3-(trifluoromethyl)pyridine-2-carbonitrileYield 67%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22609514Ethyl acetate acetateSolvent

Conditions

Temperature
65 °C

Procedure

2-cyano-5-nitro-3-trifluoromethylpyridine (7 mg, 0.032 mmol) is dissolved in 1:1 EtOAc/AcOH (1 mL) and heated to 65° C. Iron powder (9 mg, 0.161 μmol, 5 eq, 325 mesh) is added and the mixture stirred for 2 hours. The mixture is filtered through celite, and the filtrate is concentrated under vacuo. The crude residue is purified by flash chromatography on silica gel (hexane/EtOAc) to afford 4 mg (67%) of the desired product.

Workup

  1. filtrationThe mixture is filtered through celite
  2. concentrationthe filtrate is concentrated under vacuo
  3. customThe crude residue is purified by flash chromatography on silica gel (hexane/EtOAc)

Sources & evidence

ORD record
ord-51524c6e575240f690582df517a595e5
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08461343B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes