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

HRID 1403980ノート

反応式

HRID 1403980 の反応式
CN(C)/[CH:3]=[CH:4]/[C:5]1[C:15]([N+:16]([O-])=O)=[CH:14][C:13]([N+:19]([O-])=O)=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].Cl[Sn]Cl>C(O)C>[NH2:19][C:13]1[CH:12]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:5]2[CH:4]=[CH:3][NH:16][C:15]=2[CH:14]=1

参加物

4

反応物 2

HCID 24479Stannous ChlorideHCID 57470203HCID 57470203、化合物

生成物 1

HCID 53435938Ethyl 6-amino-1H-indole-4-carboxylate収率 41.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of (E)-ethyl 2-(2-(dimethylamino)vinyl)-3,5-dinitrobenzoate (11 g, 0.037 mot) 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 using sat. aq. Na2CO3 to pH 8. The precipitated solid was filtered 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 on silica gel to give ethyl 6-amino-1H-indole-4-carboxylate (3.0 g, 40%). 1HNMR (DMSO-d6) δ 10.76 (br s, 1H), 7.11-7.14 (m, 2H), 6.81-6.82 (m, 1H), 6.67-6.68 (m, 1H), 4.94 (br s, 2H), 4.32-4.25 (q, J=7.2 Hz, 2H), 1.35-1.31 (t, J=7.2, 3H); MS (ESI) m/e (M+H+) 205.0.

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
  5. filtrationThe precipitated solid was filtered
  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 on silica gel

出典と根拠

ORDレコード
ord-66c8e7a8738144d3a8928ccc61332295
出典データセット
uspto-grants-2014_12
特許番号
US08912199B2

反応ノート

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