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

HRID 34386

반응식

HRID 34386 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4e074dd19666467294a5000fc5475325
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04761412

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