8-Nitroquinoline → 3-Iodo-8-nitroquinoline

HRID 271131ノート

反応式

HRID 271131 の反応式
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].[I:14]N1C(=O)CCC1=O>C(O)(=O)C>[I:14][C:10]1[CH:11]=[N:12][C:13]2[C:8]([CH:9]=1)=[CH:7][CH:6]=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2]

参加物

4

反応物 2

HCID 118308-NitroquinolineHCID 120273N-Iodosuccinimide2 回

生成物 1

HCID 120323673-Iodo-8-nitroquinoline収率 98.2%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
62 °C

実験手順

A stirred mixture of 8-nitroquinoline (100 g, 0.57 mol) in acetic acid (500 ml) was treated with N-iodosuccinimide (155 g, 0.69 mol) portionwise over 10 minutes, and warmed to 62° C. for 6 h. A further portion of N-iodosuccinimide (25 g, 0.14 mol) was introduced and the mixture stirred for a further 16 h before cooling to ambient temperature. The solvent was removed in vacuo, keeping the temperature below 35° C. The residue was dissolved in dichloromethane (2 L) and washed successively with saturated aqueous sodium bicarbonate solution (2×1 L), 10% aqueous sodium thiosulphate solution (1 L), water (1 L), brine (100 ml), then the organic phase was dried over magnesium sulphate. The mixture was filtered and the solvent removed to give a yellow solid which was recrystallised from ethyl acetate to give the title compound (D3) (168 g, 97%) as a yellow solid;

後処理

  1. temperaturebefore cooling to ambient temperature
  2. customThe solvent was removed in vacuo
  3. customthe temperature below 35° C
  4. dissolutionThe residue was dissolved in dichloromethane (2 L)
  5. washwashed successively with saturated aqueous sodium bicarbonate solution (2×1 L), 10% aqueous sodium thiosulphate solution (1 L), water (1 L), brine (100 ml)
  6. dry with materialthe organic phase was dried over magnesium sulphate
  7. filtrationThe mixture was filtered
  8. customthe solvent removed
  9. customto give a yellow solid which
  10. customwas recrystallised from ethyl acetate

出典と根拠

ORDレコード
ord-ba7bfc0b5290448994137ca1a072f1b7
出典データセット
uspto-grants-2008_11
特許番号
US07452888B2

反応ノート

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