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

HRID 2118852노트

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HRID 2118852 반응식
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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-40 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-20f04164e4d54173a252108b3cce81ac
출처 데이터셋
uspto-grants-1987_07
특허 번호
US04680400

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