Stannous Chloride → Ethyl 6-amino-1H-indole-4-carboxylate

HRID 423766ノート

反応式

HRID 423766 の反応式
[CH2:1]([O:3][C:4](=[O:22])[C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[C:7]([N+]([O-])=O)[C:6]=1[CH:17]=[CH:18][N:19](C)C)[CH3:2].Cl[Sn]Cl>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[C:6]2[CH:17]=[CH:18][NH:19][C:7]=2[CH:8]=[C:9]([NH2:11])[CH:10]=1)=[O:22])[CH3:2]

参加物

4

反応物 2

HCID 24479Stannous ChlorideHCID 76548813HCID 76548813、化合物

生成物 1

HCID 53435938Ethyl 6-amino-1H-indole-4-carboxylate収率 40%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 2-(2-dimethylamino-vinyl)-3,5-dinitro-benzoic acid ethyl ester (11.3 g, 0.037 mol) and SnCl2 (83 g. 0.37 mol) in ethanol was heated at reflux for 4 h. The mixture was concentrated to dryness and the residue was poured into water and basified with sat. Na2CO3 solution to pH 8. The precipitate was filtered off and the filtrate was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with water (2×100 mL) and brine (150 mL), dried over Na2SO4 and concentrated to dryness. The residue was purified by column chromatography on silica gel to give 6-amino-1H-indole-4-carboxylic acid ethyl ester (B-18) (3 g, 40%). 1H NMR (DMSO-d6) δ 10.76 (br s, 1 H), 7.11-7.14 (m, 2 H), 6.81-6.82 (m, 1 H), 6.67-6.68 (m, 1 H), 4.94 (br s, 2 H), 4.32-4.25 (q,J=7.2 Hz, 2 H), 1.35-1.31 (t,J=7.2, 3 H). ESI-MS 205.0 m/z (MH+).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. concentrationThe mixture was concentrated to dryness
  4. additionthe residue was poured into water and basified with sat. Na2CO3 solution to pH 8
  5. filtrationThe precipitate was filtered off
  6. extractionthe filtrate was extracted with ethyl acetate (3×100 mL)
  7. washThe combined extracts were washed with water (2×100 mL) and brine (150 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated to dryness
  10. customThe residue was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-70638cd6c3414d9cb906e407020e5523
出典データセット
uspto-grants-2012_01
特許番号
US08101767B2

反応ノート

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