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

HRID 2190861
Notes
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Reaction equation

HRID 2190861 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-7f6e7003faa9495794e556c513476227
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08324387B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes