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

HRID 354054노트

반응식

HRID 354054 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

HCID 14939320Methyl 7-aminobenzofuran-4-carboxylate수율 88.1%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-552ff75ebe944761a6c6c026da337dcb
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756395B2

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