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8-Chloro-4-oxo-1,4-dihydro-2,5-quinolinedicarboxylic acid → 4-Oxo-1,4-dihydro-2,5-quinolinedicarboxylic acid

HRID 272565
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HRID 272565 반응식
Cl[C:2]1[C:11]2[NH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8][C:7](=[O:15])[C:6]=2[C:5]([C:16]([OH:18])=[O:17])=[CH:4][CH:3]=1>[OH-].[K+].[Pd]>[O:15]=[C:7]1[C:6]2[C:5]([C:16]([OH:18])=[O:17])=[CH:4][CH:3]=[CH:2][C:11]=2[NH:10][C:9]([C:12]([OH:14])=[O:13])=[CH:8]1
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참가 물질

4

반응물 1

HCID 589597088-Chloro-4-oxo-1,4-dihydro-2,5-quinolinedicarboxylic acid

생성물 1

HCID 104897874-Oxo-1,4-dihydro-2,5-quinolinedicarboxylic acid

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 14797Potassium Hydroxide용매

실험 절차

To a solution of 25 (7.90 g, 29.5 mmol) in 10% aqueous KOH solution (100 mL) was added 10% Pd/C (0.500 g). The reaction mixture was hydrogenated (50 psi) on a Parr hydrogenation apparatus at room temperature for 4 h. The catalyst was filtered off on a pad of celite and the filtrate was acidified with 2N HCl to pH=6.5, where a solid precipitated and was collected through a filtration. The solid was washed with H2O (100 mL) and Et2O (100 mL), and dried in vacuum at 60° C. to give an off-white solid (26, 6.79 g, 98.6%). 1H NMR (DMSO-d6, 300 MHz) δ ?8.12 (d, J=8.2 Hz, 1H), 7.76 (t, J=8.2 Hz, 1H), 7.48 (d, J=8.2 Hz, 1H), 6.74 (s, 1H).

후처리

  1. customat room temperature
  2. customfor 4 h
  3. filtrationThe catalyst was filtered off on a pad of celite
  4. customprecipitated
  5. filtrationwas collected through a filtration
  6. washThe solid was washed with H2O (100 mL) and Et2O (100 mL)
  7. customdried in vacuum at 60° C.
  8. customto give an off-white solid (26, 6.79 g, 98.6%)

출처 및 근거

ORD 기록
ord-1185c03c45504833a4a1e816ed656bcc
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07456178B2

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