Methyl 5-nitrothiophene-3-carboxylate → Methyl 5-aminothiophene-3-carboxylate

HRID 450031

반응식

HRID 450031 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([N+:10]([O-])=O)[S:7][CH:6]=1)=[O:4]>C(O)(=O)C.[Fe]>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([NH2:10])[S:7][CH:6]=1)=[O:4]

참가 물질

4

반응물 1

HCID 2740231Methyl 5-nitrothiophene-3-carboxylate

생성물 1

HCID 18983626Methyl 5-aminothiophene-3-carboxylate수율 24%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매

실험 절차

To a solution of 5-nitro-thiophene-3-carboxylic acid methyl ester (0.5 g, 2.67 mmol) in aqueous acetic acid (5 ml) was added iron powder (1.04 g, 18.6 mmol) and the reaction mixture was heated to reflux for 3 hr. The reaction mixture was filtered and triethylamine was added to the filtrate. The compound was extracted with ethyl acetate and the organic layer was washed with water, concentrated and dried to yield crude compound. The compound was purified by silica gel column chromatography, using ethyl acetate/hexane as eluent, to yield 5-amino-thiophene-3-carboxylic acid methyl ester (0.1 g, 24%).

후처리

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 3 hr
  3. filtrationThe reaction mixture was filtered
  4. additiontriethylamine was added to the filtrate
  5. extractionThe compound was extracted with ethyl acetate
  6. washthe organic layer was washed with water
  7. concentrationconcentrated
  8. customdried
  9. customto yield crude compound
  10. customThe compound was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-8665354c5f57499a8919b68a4dabffcf
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486962B2

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