Stannous chloride dihydrate → methyl (2E)-3-(3,4-diaminophenyl)prop-2-enoate

HRID 1713935ノート

反応式

HRID 1713935 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][C:3]=1[N+:14]([O-])=O.O.O.[Sn](Cl)Cl>C(O)C>[NH2:14][C:3]1[CH:4]=[C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:7][C:2]=1[NH2:1]

参加物

4

反応物 2

HCID 61436Stannous chloride dihydrateHCID 70314200Methyl (2E)-3-(4-amino-3-nitrophenyl)prop-2-enoate

生成物 1

HCID 53486922methyl (2E)-3-(3,4-diaminophenyl)prop-2-enoate収率 57%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of methyl (2E)-3-(4-amino-3-nitrophenyl)acrylate (from Step 2, 1 eq) in ethanol (0.2 M) was added tin(II) chloride dihydrate (5.75 eq). The reaction mixture was heated to reflux for 8 h. At this time the reaction was allowed to cool to RT, concentrated and diluted with EtOAc. A saturated aqueous solution of NaHCO3 was added slowly. The mixture was stirred for 20 min; the organic layer was washed with brine, dried over Na2SO4 filtered and evaporated in vacuo. The residue was purified by flash chromatography (SiO2; 70% EtOAc in PE) to afford the title compound (57%). 1H-NMR (400 MHz; DMSO-<d6, 300 K) δ 3.67 (s, 3H), 4.59 (s, 2H), 5.17 (s, 2H), 6.08 (d, J 15.6, 1H), 6.5 (d, J 8.0, 1H), 6.74 (d, J 7.6, 1H), 6.82 (s, 1H), 7.39 (d, J 15.6, 1H); MS (ES+) m/z 193 (M+H)+.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 8 h
  3. concentrationconcentrated
  4. additiondiluted with EtOAc
  5. additionA saturated aqueous solution of NaHCO3 was added slowly
  6. washthe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue was purified by flash chromatography (SiO2; 70% EtOAc in PE)

出典と根拠

ORDレコード
ord-470e5c6e7ae248d1aceea7284905a5fe
出典データセット
uspto-grants-2010_09
特許番号
US07795250B2

反応ノート

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