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

HRID 2378455Notes

Reaction equation

HRID 2378455 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]>[Au].CCOCC>[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

Participants

4

Reactant 1

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

Product 1

HCID 135322465-Amino-3-(trifluoromethyl)pyridine-2-carbonitrileYield 82%

Reagents, catalysts & solvents 2

HCID 23985GoldCatalystHCID 3283Diethyl EtherSolvent

Procedure

2-Cyano-5-nitro-3-trifluoromethylpyridine (0.065 g, 0.3 mmol) was reacted in the same manner as described in example 762D to give the desired compound 763E (0.046 g, 82%) as a gold colored solid after trituration with ether. HPLC: 100% at 2.07 min(YMC S5 ODS column) eluting with 10-90% aqueous methanol containing 0.2% phosphoric acid over a 4 min gradient monitoring at 220 nm. MS (ES): m/z 187.82 [M+H]+.

Sources & evidence

ORD record
ord-6b846726427741b7a0f0f3ad4d975021
Source dataset
uspto-grants-2008_12
Patent number
US07470797B2

Reaction notes

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