Potassium Hydroxide → 3-Chloro-2-(nitromethyl)-5-(trifluoromethyl)pyridine

HRID 1822115Notes

Reaction equation

HRID 1822115 reaction equation
[NH2:1][CH2:2][C:3]1[C:8]([Cl:9])=[CH:7][C:6]([C:10]([F:13])([F:12])[F:11])=[CH:5][N:4]=1.ClC1C(Cl)=CC(C(F)(F)F)=CN=1.C([O-:30])(C)(C)C.[K+].C([O-])(C)(C)C.[Na+].[OH-:38].[K+]>CS(C)=O.[N+](C)([O-])=O>[Cl:9][C:8]1[C:3]([CH2:2][N+:1]([O-:30])=[O:38])=[N:4][CH:5]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:7]=1

Participants

8

Reactant 5

HCID 14797Potassium HydroxideHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 11085087(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)methanamineHCID 23665647Potassium tert-butoxideHCID 23676156Sodium t-butoxide

Product 1

HCID 573712083-Chloro-2-(nitromethyl)-5-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6375NitromethaneSolvent

Procedure

The process according to the present invention is particularly suitable for the preparation of 2-aminomethyl-3-chloro-5-trifluoromethylpyridine, by reaction of in the first step 2,3-dichloro-5-trifluoromethylpyridine with nitromethane in the presence of potassium tert-butanolate, sodium tert-butanolate, or potassium hydroxide in DMSO as diluent to give 3-chloro-2-nitromethyl-5-trifluoromethylpyridine, which in the second step is hydrogenated in hydrochloric acid using palladium on carbon as catalyst to yield 3-chloro-2-aminomethyl-5-trifluoromethylpyridine.

Sources & evidence

ORD record
ord-9e832f525b9a473ba77ccac1ad296f1e
Source dataset
uspto-grants-2009_10
Patent number
US07608720B2

Reaction notes

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