Methyl 4-iodo-3-nitrobenzoate → Methyl 3-amino-4-iodobenzoate

HRID 400603

反応式

HRID 400603 の反応式
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([I:10])=[C:6]([N+:11]([O-])=O)[CH:5]=1>C(O)(=O)C.[Fe]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([I:10])=[C:6]([NH2:11])[CH:5]=1

参加物

4

反応物 1

HCID 297884Methyl 4-iodo-3-nitrobenzoate

生成物 1

HCID 21628210Methyl 3-amino-4-iodobenzoate収率 88.8%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒

反応条件

温度
80 °C

実験手順

A solution of 4-iodo-3-nitrobenzoic acid methyl ester (2.0 g, 6.50 mmol) in 25 mL of absolute alcohol and 15 mL of glacial acetic acid was treated with iron powder (3.6 g, 65.0 mmol) and the mixture was heated at 80° C. After 1 hour, the reaction mixture was filtered through a pad of silica, washed with ethanol, and concentrated in vacuo. The residue was diluted with a solution of potassium carbonate and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 1.6 g of 3-amino-4-iodobenzoic acid methyl ester as a white solid (88% yield).

後処理

  1. filtrationthe reaction mixture was filtered through a pad of silica
  2. washwashed with ethanol
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with a solution of potassium carbonate
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7d5b4f8cd506480dacb0dc38b550ddf1
出典データセット
uspto-grants-2014_06
特許番号
US08741897B2

関連ノート

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