Citric Acid → 2-(4-(4-Amino-2-nitrophenoxy)-2,3-dimethylphenyl)acetic acid

HRID 2423287ノート

反応式

HRID 2423287 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([CH3:12])[C:3]=1[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+].F[C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][C:22]=1[N+:28]([O-:30])=[O:29].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O.O>[NH2:25][C:24]1[CH:26]=[CH:27][C:21]([O:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([CH3:12])[C:3]=2[CH3:13])=[C:22]([N+:28]([O-:30])=[O:29])[CH:23]=1

参加物

7

反応物 4

HCID 311Citric AcidHCID 10796Cesium carbonateHCID 677684-Fluoro-3-nitroanilineHCID 598647702-(4-Hydroxy-2,3-dimethylphenyl)acetic acid

生成物 1

HCID 598648252-(4-(4-Amino-2-nitrophenoxy)-2,3-dimethylphenyl)acetic acid

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

Under an N2 atmosphere, 2-(4-hydroxy-2,3-dimethylphenyl)acetic acid (0.780 g, 4.33 mmol) was dissolved in DMSO (29 mL). Cesium carbonate (3.53 g, 10.8 mmol) was added and the reaction was allowed to stir at room temperature for 5 min. 4-Fluoro-3-nitroaniline (0.678 g, 4.33 mmol) was added and the reaction was heated to 80° C. for 2.25 h. The reaction was allowed to cool to room temperature and diluted with water. Citric acid was added to pH 4 and the reaction was extracted with ethyl acetate. The layers were separated and the aqueous layer was washed with additional ethyl acetate. The organics were combined, dried (Na2SO4), filtered, and concentrated in vacuo. Flash column chromatography of the residue, eluting with 0% to 8% methanol in dichloromethane, afforded the title compound. LC-MS ESI (pos.) m/z: 317.2 (M+H).

後処理

  1. temperaturethe reaction was heated to 80° C. for 2.25 h
  2. temperatureto cool to room temperature
  3. extractionthe reaction was extracted with ethyl acetate
  4. customThe layers were separated
  5. washthe aqueous layer was washed with additional ethyl acetate
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. washFlash column chromatography of the residue, eluting with 0% to 8% methanol in dichloromethane

出典と根拠

ORDレコード
ord-f366ac2c3cef43c8884261cff646ce87
出典データセット
uspto-grants-2011_06
特許番号
US07960567B2

反応ノート

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