p-Toluenesulfonic acid → Ethyl 4-hydroxy-8-iodoquinoline-3-carboxylate

HRID 1864176

반응식

HRID 1864176 반응식
C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O[C:15](=[O:31])[C:16](=[CH:22][NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[I:30])[C:17]([O:19][CH2:20][CH3:21])=[O:18])C>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:20]([O:19][C:17]([C:16]1[C:15](=[O:31])[C:29]2[C:24](=[C:25]([I:30])[CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)=[O:18])[CH3:21]

참가 물질

4

반응물 2

HCID 6101p-Toluenesulfonic acidHCID 10762902Diethyl 2-((2-iodophenylamino)methylene)malonate

생성물 1

HCID 12403679Ethyl 4-hydroxy-8-iodoquinoline-3-carboxylate수율 46%

시약·촉매·용매 1

HCID 7583Diphenyl Ether용매2회

실험 절차

In a 2-neck round bottomed flask (250 mL), phenylether (60 mL) was put to reflux on a heating mantel. When it started boiling, p-toluenesulfonic acid (0.140 g) was added. 2-[(2-iodo-phenylamino)-methylene]-malonic acid diethyl ester was dissolved in phenylether (20 mL) and the mixture was poured into the boiling solvent. The mixture was refluxed for 3 h. The crude was transferred to a bequer and cooled to room temperature. Hexanes (600 mL) were added and a precipitate was observed. The mixture was stirred for 5 min, followed by filtration of the solid and thorough wash with hexanes to afford 8-iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester as a grayish solid (2 g, 46%). 1H NMR (DMSO-d6, 400MHz) δ 1.43 (t, 3H), 4.39 (q, 2H), 7.36 (t, 1H), 8.32 (d, 1H), 8.37 (d, 1H), 8.63 (s, 1H), 11.4 (s, 1H). Exact mass calculated for C12H10INO3 342.97, found 343.9 (MH+).

후처리

  1. temperatureto reflux on a heating mantel
  2. additionthe mixture was poured into the boiling solvent
  3. temperatureThe mixture was refluxed for 3 h
  4. filtrationfollowed by filtration of the solid
  5. washthorough wash with hexanes

출처 및 근거

ORD 기록
ord-ba9644a77b19470482f8cc169586e030
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07625906B2

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