Bromine → 3,3'-Dimethoxy-2,2'-biquinoline

HRID 258408

反応式

HRID 258408 の反応式
C[Sn](C)(C)[C:3]1[C:12]([O:13][CH3:14])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.Br[C:18]1[C:27]([O:28][CH3:29])=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1.[Sn].BrBr>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:14][O:13][C:12]1[C:3]([C:18]2[C:27]([O:28][CH3:29])=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

参加物

7

反応物 4

HCID 24408BromineHCID 5352426Tin atomHCID 129587452-Bromo-3-methoxyquinolineHCID 197377152-Trimethylstannyl-3-methoxyquinoline

生成物 1

HCID 148327633,3'-Dimethoxy-2,2'-biquinoline

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 1140Toluene溶媒

実験手順

Toluene is distilled over LiAlH4 and made absolute in this manner directly before reaction. Under argon inert gas, 0.79 (2.46 mmol) of the 2-trimethylstannyl-3-methoxyquinoline described above is taken up in 5 ml of absolute toluene. 0.61 g (2.51 mmol) of 2-bromo-3-methoxyquinoline is then added to this solution. The reaction solution has a yellow color. To [sic] 20 mg (0.017 mmol) of tetrakis(triphenylphosphine) palladium(O) are then added to the reaction solution, and the reaction is monitored by thin-layer chromatography (silica gel/Et2O). The reaction solution is heated to boiling. After a reaction time of 20 hours, the tin compound and the bromine compound can still be detected. At the same time, a new band having an RF value of 0.25 and yellow fluorescence, which can be assigned to the desired product, can be detected. After a reaction time of 50 hours, another 0.010 g (0.008 mmol) of catalyst is added. After a total reaction time of 75 hours, the reaction is finally stopped. The educt can no longer be detected in the thin-layer chromatogram. The dark brown reaction solution obtained is filtered. A brownish precipitate remains and a reddish brown solution is obtained. This solution is evaporated on a rotary evaporator and taken up in diethyl ether. The reaction mixture is separated on a silica gel column using diethyl ether as the eluent. Five charges are obtained, of which the first is triphenylphosphine, the second a decomposition product of the organotin compound having a blue fluorescence, the third is 2-bromo-3-methoxyquinoline, the fourth is a small amount of a non-identified by-product and the fifth is 3,3'-dimethoxy-2,2'-biquinoline.

後処理

  1. distillationToluene is distilled over LiAlH4
  2. custommade absolute in this manner directly before reaction
  3. temperatureThe reaction solution is heated to boiling
  4. customAfter a reaction time of 20 hours

出典と根拠

ORDレコード
ord-c7eddbe4c8064ca49989cf0a8403f27f
出典データセット
uspto-grants-1993_11
特許番号
US05266700

関連ノート

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