Benzene → 1-(2-Aminophenyl)-6-bromo-1,2,3,4-tetrahydroquinoline maleate

HRID 4040

反応式

HRID 4040 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-])=O)[CH2:7][CH2:6][CH2:5]2.C1C=CC=CC=1.C(O)C.[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34]>CCOCC.[Pt]>[C:30]([OH:37])(=[O:36])/[CH:31]=[CH:32]\[C:33]([OH:35])=[O:34].[NH2:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N:8]1[C:9]2[C:4](=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=2)[CH2:5][CH2:6][CH2:7]1

参加物

7

反応物 4

HCID 241BenzeneHCID 702EthanolHCID 444266Maleic AcidHCID 138129286-Bromo-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline

生成物 1

HCID 704069761-(2-Aminophenyl)-6-bromo-1,2,3,4-tetrahydroquinoline maleate収率 55%

試薬・触媒・溶媒 2

HCID 23939Platinum触媒HCID 3283Diethyl Ether溶媒

実験手順

A Parr hydrogenation bottle was charged with 6-bromo-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline (16.7 g, 0.050 mole), 1% platinum-on-carbon (1 g), benzene (100 ml) and ethanol (100 ml). The mixture was shaken under an initial hydrogen pressure of 58 psi until uptake ceased. The mixture was then filtered to remove the catalyst and the filtrate was concentrated under vacuum. The residue was taken up in hot ether (150 ml), filtered, and the filtrate was treated with a hot solution of maleic acid (6.4 g, 0.055 mole) in ether (500 ml). The solution was boiled down to about 300 ml and allowed to cool. The supernatant was decanted from an oil, which separated. The supernatant was concentrated and the process was repeated several times to give 11.4 g (55%) of product. Recrystallization from ethyl acetate afforded the analytical sample, mp 113°-116° C.

後処理

  1. filtrationThe mixture was then filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated under vacuum
  4. filtrationfiltered
  5. temperatureto cool
  6. customThe supernatant was decanted from an oil, which
  7. customseparated
  8. concentrationThe supernatant was concentrated

出典と根拠

ORDレコード
ord-2b04d48d5e5a4e3d9c091e3fa05cb57e
出典データセット
uspto-grants-1988_02
特許番号
US04723007

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