3-(Trifluoromethyl)aniline → STK345463

HRID 238499Notes

Reaction equation

HRID 238499 reaction equation
[Cl:1][C:2]1[C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[F:11][C:12]([F:21])([F:20])[C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]([NH:16][C:15]2[CH:17]=[CH:18][CH:19]=[C:13]([C:12]([F:11])([F:20])[F:21])[CH:14]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 81531DiisopropylethylamineHCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 683662STK345463Yield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Chloropyridine-3-carbonyl chloride (18.02 g, 0.102 mol) in CH2Cl2 (100 ml) was added dropwise (via an addition funnel) to a stirred solution of 3-(trifluoromethyl)-aniline (15.00 g, 0.093 mol) and DIEA (24.39 ml, 0.14 mol) in CH2Cl2 (500 ml) at 0° C. The mixture gradually was warmed to RT. The reaction continued for 18 h before washing several times with saturated NaHCO3 aqueous solution and brine, respectively. The organic layer was dried over Na2SO4 and evaporated. The resulting oil was purified over silica gel with EtOAc/hexane (2:1) as eluant to leave the amide as a white solid (26.08 g). MS: (ES+) 301 (M+1)+; (ES−): 299 (M−1)−. Calc'd for C13H8ClF3N2O: 300.03.

Workup

  1. washbefore washing several times with saturated NaHCO3 aqueous solution and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated
  4. customThe resulting oil was purified over silica gel with EtOAc/hexane (2:1) as eluant

Sources & evidence

ORD record
ord-285ae9fe542745049c71d43e7b345f8f
Source dataset
uspto-grants-2014_02
Patent number
US08642624B2

Reaction notes

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