Hydrogen Peroxide → 1,2,3,4-Tetrahydro-6-iodoquinoline

HRID 710306ノート

反応式

HRID 710306 の反応式
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[I:11]I.OO>O>[I:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[NH:1][CH2:2][CH2:3][CH2:4]2

参加物

5

反応物 3

HCID 784Hydrogen PeroxideHCID 807IodineHCID 694601,2,3,4-Tetrahydroquinoline

生成物 1

HCID 289765451,2,3,4-Tetrahydro-6-iodoquinoline収率 100.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixture of 1,2,3,4,-tetrahydroquinoline (0.34 g; 2.55 mmol) and I2 (0.32 g; 1.27 mmol) in H2O (10 ml), 30% H2O2 (0.26 ml; 2.55 mmol) was added at room temperature. The resulting mixture was vigorously stirred overnight at room temperature, and then extracted with Et2O (2×15 ml). The combined organic phase was washed with H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2; CH2Cl2), to give the title compound (0.33 g; 50%) as a creamy syrup. 1H-NMR (CDCl3) 1.84-1.92 (m, 2H); 2.69 (tr, 2H, J=6.4 Hz); 3.27 (tr, 2H, J=6.4 Hz); 3.82 (broad s, 1H); 6.22 (d, 1H, J=8.2 Hz); 7.15-7.21 (m, 2H).

後処理

  1. additionwas added at room temperature
  2. extractionextracted with Et2O (2×15 ml)
  3. washThe combined organic phase was washed with H2O, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customthe residue was purified by FCC (SiO2; CH2Cl2)

出典と根拠

ORDレコード
ord-43265e7603ad43aaa088974e93f33a58
出典データセット
uspto-grants-2015_11
特許番号
US09181182B2

反応ノート

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