Sulfuric Acid → 5,6,7-Trimethylquinoline-8-carboxaldehyde

HRID 2118852ノート

反応式

HRID 2118852 の反応式
C([Li])CCC.Br[C:7]1[C:8]([CH3:19])=[C:9]([CH3:18])[C:10]([CH3:17])=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2.[CH:20](N1CCCCC1)=[O:21].S(=O)(=O)(O)O.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH3:17][C:10]1[C:9]([CH3:18])=[C:8]([CH3:19])[C:7]([CH:20]=[O:21])=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2

参加物

7

反応物 5

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 174291-PiperidinecarboxaldehydeHCID 139354168-Bromo-5,6,7-trimethylquinolineHCID 178418339Butyllithium

生成物 1

HCID 139353385,6,7-Trimethylquinoline-8-carboxaldehyde

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-40 °C

実験手順

n-Butyl lithium (2.1 equiv; 1.55M in hexane) was added slowly to a suspension of 8-bromo-5,6,7-trimethylquinoline (4.2 g) in anhydrous THF (40 ml) under nitrogen at -90° C. After 3 hr a solution of N-formylpiperidine (2.1 equiv) in anhydrous THF (10 ml) was added to the mixture was warmed to -40° C. over ca. 2 hr. A dilute sulfuric acid solution (1N; 20 ml) was added and the mixture was warmed to room temperature. The mixture was made basic by the addition of potassium carbonate and was then extracted with ether. The dried (MgSO4) organic fraction was evaporated and the residue was purified by column chromatography over alumina with carbon tetrachloride/dichloromethane (1:1 v/v) elution to give 5,6,7-trimethylquinoline-8-carboxaldehyde as a pale yellow solid, mp 162° C. Pmr specturm (CDCl3 ; δ in ppm): 2.48 (3H,s); 2.68 (3H,s); 2.74 (3H,s); 7.43-8.96 (3H,m); 11.61 (1H,s).

後処理

  1. temperaturethe mixture was warmed to room temperature
  2. extractionwas then extracted with ether
  3. dry with materialThe dried (MgSO4) organic fraction
  4. customwas evaporated
  5. customthe residue was purified by column chromatography over alumina with carbon tetrachloride/dichloromethane (1:1 v/v) elution

出典と根拠

ORDレコード
ord-20f04164e4d54173a252108b3cce81ac
出典データセット
uspto-grants-1987_07
特許番号
US04680400

反応ノート

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