Methanol → HCID 68505396、化合物

HRID 1808336ノート

反応式

HRID 1808336 の反応式
S(Cl)(Cl)=O.[NH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][C:16]([OH:18])=[O:17])[CH:13]=2)[CH2:8][CH2:7][CH2:6]1.[CH3:19]O>>[NH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:13]=2)[CH2:8][CH2:7][CH2:6]1

参加物

4

反応物 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 39733728HCID 39733728、化合物

生成物 1

HCID 68505396HCID 68505396、化合物

反応条件

温度
70 °C

実験手順

Thionyl chloride (13 g; 1.5 equiv.) was added dropwise at 0° C., in the course of 5-10 minutes, to a solution of crude 2-(1,2,3,4-tetrahydroquinolin-7-yl)acetic acid (stage 5; 14 g; 1 equiv.) in 140 ml of methanol, and the resulting reaction mixture was then heated for 6 hours at reflux (70° C.). When the conversion was complete, the reaction solution was concentrated under reduced pressure and the residue was taken up in 150 ml of water, rendered basic (pH 7-8) with sodium carbonate and finally extracted with 2×150 ml of chloroform. The combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 10-12% ethyl acetate/-hexane). Methyl 2-(1,2,3,4-tetrahydroquinolin-7-yl)acetate (4 g) was obtained in the form of a colorless oil.

後処理

  1. customthe resulting reaction mixture
  2. temperaturewas then heated for 6 hours
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. extractionfinally extracted with 2×150 ml of chloroform
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography (silica gel, 10-12% ethyl acetate/-hexane)

出典と根拠

ORDレコード
ord-9e34484fea0f45db8bcc923e6f984592
出典データセット
uspto-grants-2013_01
特許番号
US08357717B2

反応ノート

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