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

HRID 4101

Reaction equation

HRID 4101 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 106861,2,3-TrimethylbenzeneSolvent

Procedure

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 solvent 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 l) 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 gel. 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.

Workup

  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 gel
  8. washElution with 1:1 hexane

Sources & evidence

ORD record
ord-e4d5655a3184459db8a25be7ea081d4a
Source dataset
uspto-grants-1988_02
Patent number
US04723003

Linked notes

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