Methyl iodide → Methyl 4-(methyl(phenyl)amino)benzoate

HRID 1177853ノート

反応式

HRID 1177853 の反応式
CI.[CH3:3][N:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1.[C:20]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:20][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:5]([N:4]([CH3:3])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 232051694-(Methyl(phenyl)amino)benzoic acid

生成物 1

HCID 12138924Methyl 4-(methyl(phenyl)amino)benzoate収率 75%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Methyl iodide (227 mg, 0.1 mL, 1.68 mmol) was added drop wise to a suspension of 4-(Methyl-phenyl-amino)-benzoic acid (120 mg, 0.56 mmol) and K2CO3 in DMF (5 mL). The resulting mixture was heated at 80° C. with stirring overnight. The mixture was filtered, cold water was then added, and the product was extracted with EtOAc. The organic layer was washed with saturated brine solution and dried over Na2SO4. The organic layer was then concentrated under reduced pressure to get the residue The obtained residue was purified by column chromatography (using silica gel of 60-120 mesh and 5% EtOAc in Hexane as eluent) to afford 85 mg (75% yield) of 4-(Methyl-phenyl-amino)-benzoic acid methyl ester. 1H-NMR (CDCl3): δ 7.8 (d, 2H), 7.4 (T, 2H), 7.2 (m, 2H), 6.8 (d, 2H), 3.8 (s, 3H), 3.2 (s, 3H).

後処理

  1. filtrationThe mixture was filtered
  2. additioncold water was then added
  3. extractionthe product was extracted with EtOAc
  4. washThe organic layer was washed with saturated brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationThe organic layer was then concentrated under reduced pressure
  7. customto get the residue The obtained residue
  8. customwas purified by column chromatography (using silica gel of 60-120 mesh and 5% EtOAc in Hexane as eluent)

出典と根拠

ORDレコード
ord-89ae0cb2e15546cc9fc6fb1fac18740e
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

反応ノート

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