Triethylamine → N-[2-hydroxy-5-(trifluoromethyl)phenyl]-3 (methoxymethyl)isonicotinamide

HRID 1913747Notes

Reaction equation

HRID 1913747 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[OH:12].[CH3:13][O:14][CH2:15][C:16]1[CH:24]=[N:23][CH:22]=[CH:21][C:17]=1[C:18](O)=[O:19].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>O.CN(C=O)C>[OH:12][C:3]1[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=1[NH:1][C:18](=[O:19])[C:17]1[CH:21]=[CH:22][N:23]=[CH:24][C:16]=1[CH2:15][O:14][CH3:13]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 1202462-Amino-4-(trifluoromethyl)phenolHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 581481933-(Methoxymethyl)isonicotinic acid

Product 1

HCID 66880004N-[2-hydroxy-5-(trifluoromethyl)phenyl]-3 (methoxymethyl)isonicotinamideYield 86.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.40 g of 2-amino-4-(trifluoromethyl)phenol, 0.38 g of 3-methoxymethyl isonicotinic acid, 1.30 g of BOP reagent, 0.30 g of triethylamine, and 20 ml of DMF was stirred at room temperature for four hours. Water was added to the reaction mixture, and the reaction mixture was extracted with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.64 g of N-[2-hydroxy-5-(trifluoromethyl)phenyl]-3(methoxymethyl)isonicotinamide.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate twice
  2. washThe combined organic layers were washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-41dc7481be0e4ee3810ec4ddc01383e6
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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