Isatin → 3-Methyl-2-phenylquinoline-4-carboxylic acid

HRID 1071835노트

반응식

HRID 1071835 반응식
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[C:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=O)[CH2:13][CH3:14].[OH-:22].[K+]>C(O)C.O>[CH3:14][C:13]1[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:1][C:11]2[C:6]([C:4]=1[C:2]([OH:22])=[O:3])=[CH:7][CH:8]=[CH:9][CH:10]=2

참가 물질

6

반응물 3

HCID 7054IsatinHCID 71481-Phenyl-1-propanoneHCID 14797Potassium Hydroxide

생성물 1

HCID 6737103-Methyl-2-phenylquinoline-4-carboxylic acid수율 85%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

A solution of isatin (5.00 g, 34.0 mmol), propiophenone (5.47 g, 5.43 mL, 40.8 mmol), and potassium hydroxide pellets (6.73 g, 102 mmol) in ethanol (40 mL) was stirred at reflux for 23 h. After cooling, the solvent was removed in vacuo to give a brown residue. The residue was dissolved in water (75 mL) and washed with diethyl ether (4×100 mL). The aqueous layer was cooled by the addition of ice (˜50 g) and acidified to pH˜1 via dropwise addition of concentrated HCl with stirring. A solid precipitate was collected by filtration, washed with water and dried to provide the title compound as a yellowish-tan solid (7.59 g, 85%), which was used without further purification. MS (API+): M+1: 264 (45%), 220 (100); %); 1H NMR (300 MHz, DMSO-d6) d 2.39 (s, 3H), 7.49-7.57 (m, 3H), 7.59-7.72 (m, 7.76-7.84 (m, 2H), 8.06 (d, J=8.5 Hz, 1H), 14.20 (v br s, 1H, exchangeable).

후처리

  1. temperatureat reflux for 23 h
  2. temperatureAfter cooling
  3. customthe solvent was removed in vacuo
  4. customto give a brown residue
  5. washwashed with diethyl ether (4×100 mL)
  6. temperatureThe aqueous layer was cooled by the addition of ice (˜50 g)
  7. additionacidified to pH˜1 via dropwise addition of concentrated HCl
  8. filtrationA solid precipitate was collected by filtration
  9. washwashed with water
  10. customdried

출처 및 근거

ORD 기록
ord-9961680a2fa6484eaec9794223c9a1cb
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06906193B2

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