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

HRID 400603

반응식

HRID 400603 반응식
[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

참가 물질

4

반응물 1

HCID 297884Methyl 4-iodo-3-nitrobenzoate

생성물 1

HCID 21628210Methyl 3-amino-4-iodobenzoate수율 88.8%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7d5b4f8cd506480dacb0dc38b550ddf1
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741897B2

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