Stannous chloride dihydrate → Methyl 7-aminobenzofuran-4-carboxylate

HRID 354054ノート

反応式

HRID 354054 の反応式
O.O.[Sn](Cl)Cl.[CH3:6][O:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]([N+:19]([O-])=O)=[C:14]2[O:18][CH:17]=[CH:16][C:15]=12)=[O:9]>C(OCC)(=O)C.C(O)C>[CH3:6][O:7][C:8]([C:10]1[CH:11]=[CH:12][C:13]([NH2:19])=[C:14]2[O:18][CH:17]=[CH:16][C:15]=12)=[O:9]

参加物

5

反応物 2

HCID 61436Stannous chloride dihydrateHCID 20738655Methyl 7-nitrobenzofuran-4-carboxylate

生成物 1

HCID 14939320Methyl 7-aminobenzofuran-4-carboxylate収率 88.1%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Tin (II) chloride dihydrate (15.0 g, 66.5 mmol) was added to a suspension of 7-nitro-benzofuran-4-carboxylic acid methyl ester (4.82 g, 21.8 mmol) in ethyl acetate (80 mL) and ethanol (80 mL). The reaction mixture was stirred at room temperature for four days then partitioned between ethyl acetate and saturated aqueous solution of potassium carbonate. The organic extract was washed with brine, dried (anhydrous sodium sulfate) and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel eluting with 30% ethyl acetate in hexane give 7-amino-benzofuran-4-carboxylic acid methyl ester (3.67 g, 88%). 1H NMR (CDCl3) δ: 3.92 (s, 3H), 6.60 (d, 1H, J=8.2 Hz), 7.34 (d, 1H, J=2.1 Hz), 7.67 (d, 1H, J=2.1 Hz), 7.84 (d, 1H, J=8.2 Hz).

後処理

  1. customthen partitioned between ethyl acetate and saturated aqueous solution of potassium carbonate
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried (anhydrous sodium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography over silica gel eluting with 30% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-552ff75ebe944761a6c6c026da337dcb
出典データセット
uspto-grants-2004_06
特許番号
US06756395B2

反応ノート

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