4-Nitrophenol → 4-Nitrophenyl 2-{[3-(trifluoromethyl)phenyl]amino}nicotinate

HRID 1063535Notes

Reaction equation

HRID 1063535 reaction equation
[CH:1]1[CH:2]=[C:3]([C:17]([F:20])([F:19])[F:18])[CH:4]=[C:5]([NH:7][C:8]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([OH:16])=[O:15])[CH:6]=1.[N+:21]([C:24]1[CH:29]=[CH:28][C:27](O)=[CH:26][CH:25]=1)([O-:23])=[O:22].CCN=C=NCCCN(C)C>C(Cl)Cl>[F:20][C:17]([F:18])([F:19])[C:3]1[CH:4]=[C:5]([NH:7][C:8]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([O:16][C:27]2[CH:28]=[CH:29][C:24]([N+:21]([O-:23])=[O:22])=[CH:25][CH:26]=2)=[O:15])[CH:6]=[CH:1][CH:2]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 4488Niflumic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

Product 1

HCID 219481574-Nitrophenyl 2-{[3-(trifluoromethyl)phenyl]amino}nicotinateYield 31.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a warmed (40° C. ) suspension of niflumic acid (10.0 g, 35.4 mmol) and 4-nitrophenol (4.9 g, 35.4 mmol) in CH2Cl2 (80 mL) was added a suspension of EDCI (6.8 g, 35.4 mmol) in CH2Cl2 (20 mL). The reaction was stirred for 16 h, and then cooled to room temperature. The solution was quenched with water (50 mL), and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were washed with water and dried over Na2SO4. The solvent was removed in vacuo, and the residue was purified by trituration with Hex:CH2Cl2 to afford 4-Nitrophenyl 2-{[3-(trifluoromethyl)phenyl]amino}nicotinate (4.5 g, 31%): LCMS RT: 4.03 min, MH+: 404.1.

Workup

  1. temperatureTo a warmed
  2. additionwas added
  3. customThe solution was quenched with water (50 mL)
  4. extractionthe aqueous layer was extracted with CH2Cl2
  5. washThe combined organic extracts were washed with water
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by trituration with Hex

Sources & evidence

ORD record
ord-3cd0593a14ae4ffcaff3973f2e7fa043
Source dataset
uspto-grants-2005_11
Patent number
US06964971B2

Reaction notes

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