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

HRID 1827858ノート

反応式

HRID 1827858 の反応式
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]

参加物

6

反応物 2

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

生成物 1

HCID 684370112-Carboxy-4-oxo-7-methylquinoline収率 98.8%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-05b4c023314544aabf1e9a6c1ac1bf2f
出典データセット
uspto-grants-2006_06
特許番号
US07056923B2

反応ノート

読み込み中…