Cyclohexylamine → 4-Hydroxy-1,6-dimethyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid cyclohexylamide

HRID 346592노트

반응식

HRID 346592 반응식
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:10][C:11]([C:13]1[C:14](=[O:26])[N:15]([CH3:25])[C:16]2[C:21]([C:22]=1[OH:23])=[CH:20][C:19]([CH3:24])=[CH:18][CH:17]=2)=O)C>C1(C)C=CC=CC=1.O>[CH:1]1([NH:7][C:11]([C:13]2[C:14](=[O:26])[N:15]([CH3:25])[C:16]3[C:21]([C:22]=2[OH:23])=[CH:20][C:19]([CH3:24])=[CH:18][CH:17]=3)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 2

HCID 7965CyclohexylamineHCID 694760433-Quinolinecarboxylic acid,1,2-dihydro-4-hydroxy-1,6-dimethyl-2-oxo-,ethyl ester

생성물 1

HCID 694769974-Hydroxy-1,6-dimethyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid cyclohexylamide수율 97%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

Cyclohexylamine (2.85 mL, 24.95 mmol) was added to a solution of Compound 17 (3.26 g, 12.47 mmol) in toluene (50 mL) and refluxed for 4 h. The solution was cooled and the solvent was evaporated under vacuum. The residue obtained was suspended in water, briefly sonicated, and filtered. The crude product was recrystallized by ether to yield 3.8 g (97%) of white solids. M.P. 218° C. 1H NMR (DMSO-d6): δ 1.28 (m, 1H), 1.36 (m, 4H), 1.55 (m, 1H), 1.68 (m, 2H), 1.87 (m, 2H), 2.40 (s, 3H), 3.59 (s, 3H), 3.87 (m, 1H), 7.51 (d, J=8.7 Hz, 1H), 7.61 (d, J=8.7 Hz, 1H), 7.86 (s, 1H), 10.49 (s, 1H). EIMS m/z 315 (M+1), 337 (M+23).

후처리

  1. temperaturerefluxed for 4 h
  2. temperatureThe solution was cooled
  3. customthe solvent was evaporated under vacuum
  4. customThe residue obtained
  5. custombriefly sonicated
  6. filtrationfiltered
  7. customThe crude product was recrystallized by ether

출처 및 근거

ORD 기록
ord-1ba49a7ee60545ffb2d45e2846e8f771
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07173036B2

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