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

HRID 450031

反応式

HRID 450031 の反応式
[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]

参加物

4

反応物 1

HCID 2740231Methyl 5-nitrothiophene-3-carboxylate

生成物 1

HCID 18983626Methyl 5-aminothiophene-3-carboxylate収率 24%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-8665354c5f57499a8919b68a4dabffcf
出典データセット
uspto-grants-2013_07
特許番号
US08486962B2

関連ノート

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