Dimethylamine → N,N-dimethyl-5-nitro-3-(trifluoromethyl)pyridin-2-amine

HRID 731954Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([C:11]([F:14])([F:13])[F:12])[C:7](=O)[NH:8][CH:9]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.Cl[C:20]1C(C(F)(F)F)=CC([N+]([O-])=O)=[CH:22][N:21]=1.CNC>>[CH3:20][N:21]([CH3:22])[C:7]1[C:6]([C:11]([F:14])([F:13])[F:12])=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=1

Participants

Reactant 4

HCID 674Dimethylamine

HCID 24386Thionyl Chloride

HCID 27750952-Hydroxy-5-nitro-3-(trifluoromethyl)pyridine

HCID 38491402-Chloro-5-nitro-3-(trifluoromethyl)pyridine

Product 1

HCID 2727273N,N-dimethyl-5-nitro-3-(trifluoromethyl)pyridin-2-amine

Procedure

5-Nitro-3-(trifluoromethyl)pyridin-2(1H)-one was treated with thionyl chloride and then the resulting 2-chloro-5-nitro-3-(trifluoromethyl)pyridine was treated with dimethylamine to obtain N,N-dimethyl-5-nitro-3-(trifluoromethyl)pyridin-2-amine.

Sources & evidence

ORD record: ord-7d6450c59c5d4a75a7548aa77228973e
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585878B2

Reaction notes

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