Stannous chloride dihydrate → HCID 57470208、化合物

HRID 503416ノート

反応式

HRID 503416 の反応式
[C:1]([C:5]1[C:6]([N+:19]([O-])=O)=[CH:7][C:8]([N+]([O-])=O)=[C:9](/[CH:11]=[CH:12]/[N:13](C)C)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O.O.[Sn](Cl)Cl>C(O)C>[C:1]([C:5]1[CH:10]=[C:9]2[C:8](=[CH:7][C:6]=1[NH2:19])[NH:13][CH:12]=[CH:11]2)([CH3:2])([CH3:3])[CH3:4]

参加物

4

反応物 2

HCID 61436Stannous chloride dihydrateHCID 59129370HCID 59129370、化合物

生成物 1

HCID 57470208HCID 57470208、化合物収率 12%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of (E)-2-(5-tert-butyl-2,4-dinitrophenyl)-N,N-dimethylethen-amine (5.3 g, 18 mmol) and tin (II) chloride dihydrate (37 g, 0.18 mol) in ethanol (200 mL) was heated at reflux overnight. The mixture was cooled to room temperature and the solvent was removed under vacuum. The residual slurry was diluted with water (500 mL) and was basifed with 10% aq. Na2CO3 to pH 8. The resulting suspension was extracted with ethyl acetate (3×100 mL). The ethyl acetate extract washed with water and brine, dried over Na2SO4, and concentrated. The residual solid washed with CH2Cl2 to afford a yellow powder, which was purified by column chromatography to give 5-tert-butyl-1H-indol-6-amine (0.40 g, 12%). 1H NMR (DMSO-d6) δ 10.34 (br s, 1H), 7.23 (s, 1H), 6.92 (s, 1H), 6.65 (s, 1H), 6.14 (s, 1H), 4.43 (br s, 2H), 2.48 (s, 9H); MS (ESI) m/e (M+H+) 189.1.

後処理

  1. temperatureat reflux overnight
  2. customthe solvent was removed under vacuum
  3. additionThe residual slurry was diluted with water (500 mL)
  4. extractionThe resulting suspension was extracted with ethyl acetate (3×100 mL)
  5. extractionThe ethyl acetate extract
  6. washwashed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. washThe residual solid washed with CH2Cl2
  10. customto afford a yellow powder, which
  11. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-3d5f93158d6d4246912fe376a5737c06
出典データセット
uspto-grants-2010_08
特許番号
US07776905B2

反応ノート

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