Lithium hydroxide, monohydrate → 2-Carboxy-4-oxo-7-methylquinoline

HRID 1795216노트

반응식

HRID 1795216 반응식
C[O:2][C:3]([C:5]1[CH2:14][C:13](=[O:15])[C:12]2[C:7](=[C:8](Cl)[C:9]([CH3:17])=[C:10](Cl)[CH:11]=2)[N:6]=1)=[O:4].O[Li].O>CO.O.[Pd]>[C:3]([C:5]1[CH2:14][C:13](=[O:15])[C:12]2[C:7](=[CH:8][C:9]([CH3:17])=[CH:10][CH:11]=2)[N:6]=1)([OH:4])=[O:2]

참가 물질

6

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 684344222-(Methoxycarbonyl)-4-oxo-6,8-dichloro-7-methylquinoline

생성물 1

HCID 684370112-Carboxy-4-oxo-7-methylquinoline수율 98.8%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 962Water용매

실험 절차

2-(Methoxycarbonyl)-4-oxo-6,8-dichloro-7-methylquinoline (28.5 g, 99.6 mmol) was suspended in methanol (1 L) and a solution of LiOH.H2O (20.5 g, 0.5 mol) in water (200 mL) was added to the solution. The resulting reaction mixture was stirred at ambient temperature for 0.5 hours. Pd/C (5.8 g) was added to the reaction mixture and the resulting reaction mixture was shaken under 50 Psi hydrogen overnight. The reaction mixture was filtered, concentrated under reduced pressure to remove methanol, diluted with water (300 mL) and the pH was adjusted to between pH 3 and pH 4 by 2N HCl. The precipitate was collected by filtration, washed with water and dried to afford a white solid, 2-carboxy-4-oxo-7-methylquinoline (20 g, 90%); NMR (DMSO-d6) 2.40 (s, 3), 6.60 (s, 1), 7.20 (d, 1), 7.68 (s, 1), 7.96 (d, 1) ppm.

후처리

  1. customThe resulting reaction mixture
  2. customthe resulting reaction mixture
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. customto remove methanol
  6. additiondiluted with water (300 mL)
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with water
  9. customdried

출처 및 근거

ORD 기록
ord-bc199ff025e244ea823b59622ce677e2
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07026323B2

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