Sodium Hydroxide → 6-Bromo-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline

HRID 34386

反応式

HRID 34386 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)([O-:3])=[O:2].[Br:20]N1C(=O)CCC1=O.[OH-].[Na+]>CN(C)C=O>[Br:20][C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][CH:17]=1)[N:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:11][CH2:12][CH2:13]2

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 138129261-(2-Nitrophenyl)-1,2,3,4-tetrahydroquinoline

生成物 1

HCID 138129286-Bromo-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline収率 82.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A stirred solution, under nitrogen, of 1-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline (76.3 g, 0.30 mole) in dimethylformamide (1000 ml) was cooled to -10° C. A solution of of N-bromosuccinimide(58.7 g, 0.33 mole) in dimethylformamide (250 ml) was added dropwise at such a rate as to keep the reaction temperature below 0° C. (1.5 hours). Half-an hour after the addition was completed, the reaction mixture was poured into 7 liters of 2N-sodium hydroxide solution/ice, with stirring. The product separated as an oil. The quench fluids were decanted and the oil was rinsed several times with water. The oil was dissolved in dichloromethane (1.5 1). The organic solution was extracted once with 2N-sodium hydroxide solution, thrice with water, dried over sodium sulfate and concentrated. The residue was dissolved in 1:1 hexane:toluene (250 ml) and the solution was adsorbed on a chromatography column containing 2 kg of silica gel packed in 1:1 hexane:toluene. Elution with this solvent mixture provided 82.7 g (82%) of product, as an oil. For analysis, a sample was Kugelrohr distilled at a vessel temperature of 166°-168° C. (0.2 mm Hg).

後処理

  1. customthe reaction temperature below 0° C. (1.5 hours)
  2. additionHalf-an hour after the addition
  3. customThe product separated as an oil
  4. customThe quench fluids were decanted
  5. washthe oil was rinsed several times with water
  6. dissolutionThe oil was dissolved in dichloromethane (1.5 1)
  7. extractionThe organic solution was extracted once with 2N-sodium hydroxide solution, thrice with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. dissolutionThe residue was dissolved in 1:1 hexane
  11. additioncontaining 2 kg of silica gel
  12. washElution with this solvent mixture

出典と根拠

ORDレコード
ord-4e074dd19666467294a5000fc5475325
出典データセット
uspto-grants-1988_08
特許番号
US04761412

関連ノート

読み込み中…