5-Chloro-2-nitrobenzoic acid → Ethyl 5-chloro-2-nitrobenzoate

HRID 1094984ノート

反応式

HRID 1094984 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].CO[C:16](=O)[C:17]1C=C(N(CCC)CCC)C=CC=1N.S(Cl)(Cl)=O>C(O)C>[CH2:16]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[N+:11]([O-:13])=[O:12])[CH3:17]

参加物

5

反応物 3

HCID 172865-Chloro-2-nitrobenzoic acidHCID 24386Thionyl ChlorideHCID 613136502-Amino-5-dipropylamino-benzoic acid methyl ester

生成物 1

HCID 603450Ethyl 5-chloro-2-nitrobenzoate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

5-Chloro-2-nitro-benzoic acid (compound A′) (10.0 g) was dissolved in ethanol (100 ml). Thionyl chloride (20 ml) was added dropwise to the solution at 0° C., and the mixture was then heated under reflux with stirring for 48 hr. After the completion of the reaction, the reaction solution was concentrated under the reduced pressure. Distilled water was added to the residue, and the mixture was neutralized with a saturated aqueous sodium hydrogencarbonate solution under ice cooling. The cooled solution was subjected to separatory extraction with ethyl acetate. The organic layer was dried over sodium sulfate and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 5-chloro-2-nitro-benzoic acid ethyl ester as a useful intermediate (11.0 g, yield 97%).

後処理

  1. temperaturethe mixture was then heated
  2. temperatureunder reflux
  3. customAfter the completion of the reaction
  4. concentrationthe reaction solution was concentrated under the reduced pressure
  5. additionDistilled water was added to the residue
  6. extractionThe cooled solution was subjected to separatory extraction with ethyl acetate
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. concentrationwas then concentrated under the reduced pressure
  9. customThe residue was purified by column chromatography
  10. washeluted with a chloroform-methanol system

出典と根拠

ORDレコード
ord-08c3a43aa60d4471ba4aff64c1b9ad9b
出典データセット
uspto-grants-2012_03
特許番号
US08134015B2

反応ノート

読み込み中…