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

HRID 1063535ノート

反応式

HRID 1063535 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3cd0593a14ae4ffcaff3973f2e7fa043
出典データセット
uspto-grants-2005_11
特許番号
US06964971B2

反応ノート

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