2-m-Tolyl-6-(trifluoromethyl)nicotinonitrile → (2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine

HRID 1428733Notes

Reaction equation

HRID 1428733 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:8]=2[C:9]#[N:10])[CH:2]=1>N>[C:1]1([CH3:19])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:8]([CH2:9][NH2:10])=[CH:11][CH:12]=[C:13]([C:15]([F:17])([F:16])[F:18])[N:14]=2)[CH:2]=1

Participants

3

Reactant 1

HCID 866802152-m-Tolyl-6-(trifluoromethyl)nicotinonitrile

Product 1

HCID 86680208(2-m-Tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamineYield 94%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

2-m-tolyl-6-(trifluoromethyl)nicotinonitrile (1.87 g, 7.159 mmol) was dissolved in 2 M methanolic ammonia solution (286 mL, 0.025 mmol/mL) and hydrogenated in an H-cube apparatus (10 bar, 80° C., 1 mL/min, 0.25 mol/L). After removal of the solvent under vacuum, (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine (1.787 g, 94%) was obtained as a white solid. The reaction step was repeated to afford in summary 3.61 g of (2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methanamine.

Workup

  1. customAfter removal of the solvent under vacuum

Sources & evidence

ORD record
ord-570aa44085914731b780a37a2d447b24
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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