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

HRID 34390

反応式

HRID 34390 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][CH2:13]1.N1C(C)=CC(C)=CC=1C>CC1C=CC=C(C)C=1C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14][CH2:13]2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

参加物

5

反応物 3

HCID 79532,4,6-TrimethylpyridineHCID 694601,2,3,4-TetrahydroquinolineHCID 770041,4-Dibromo-2-nitrobenzene

生成物 1

HCID 138129271-(4-Bromo-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline収率 18%

試薬・触媒・溶媒 1

HCID 106861,2,3-Trimethylbenzene溶媒

実験手順

A stirred mixture, under nitrogen, of 2,5-dibromonitrobenzene (140.5 g, 0.50 mole), 1,2,3,4-tetrahydroquinoline (133.2 g, 1.00 mole) and symmetrical collidine (121.2 g 1.00 mole) in 1,2,3-trimethylbenzene (500 ml) as solvents was heated at 160°-165° C. for 7 days. The mixture was cooled to room temperature, filtered, and the filtrate was concentrated in vacuo (100° C.). The residue was taken up in dichloromethane (1.5 1) and the solution was extracted three times with dilute hydrochloric acid, once with dilute sodium hydroxide solution, three times with water, dried over anhydrous sodium sulfate and concentrated. This residue was dissolved in 1:1 hexane:toluene (250 ml) and adsorbed on a chromatography column containing 3 kg of silica el. Elution with 1:1 hexane:toluene gave 30 g (18%) of product, as an oil. A portion of the oil was Kugelrohr distilled at an oven-temperature of 163°-165° C. (0.1 mm Hg) to provide the analytical sample.

後処理

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated in vacuo (100° C.)
  3. extractionthe solution was extracted three times with dilute hydrochloric acid
  4. dry with materialonce with dilute sodium hydroxide solution, three times with water, dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. dissolutionThis residue was dissolved in 1:1 hexane
  7. additioncontaining 3 kg of silica el
  8. washElution with 1:1 hexane

出典と根拠

ORDレコード
ord-1e47a9ff0f4d46808118082466f52e38
出典データセット
uspto-grants-1988_08
特許番号
US04761412

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