Hydrochloric Acid → 1,4-Dihydro-2-(methylthio)-4-oxo-3-quinolinecarboxylic acid

HRID 423722ノート

反応式

HRID 423722 の反応式
C([O:3][C:4]([C:6]1[C:7]([S:17][CH3:18])=[N:8][C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:5])C.Cl>[OH-].[Na+]>[CH3:18][S:17][C:7]1[NH:8][C:9]2[C:14]([C:15](=[O:16])[C:6]=1[C:4]([OH:5])=[O:3])=[CH:13][CH:12]=[CH:11][CH:10]=2

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 1784701074-Hydroxy-2-methylsulfanyl-quinoline-3-carboxylic acid ethyl ester

生成物 1

HCID 465076311,4-Dihydro-2-(methylthio)-4-oxo-3-quinolinecarboxylic acid収率 85%

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

実験手順

4-Hydroxy-2-methylsulfanyl-quinoline-3-carboxylic acid ethyl ester (8 g, 30 mmol) was heated under reflux in NaOH solution (10%, 100 mL) for 1.5 h. After cooling, the mixture was acidified with concentrated HCl to pH 4. The resulting solid was collected via filtration, washed with water (100 mL) and MeOH (100 mL) to give 2-methylsulfanyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (A-16) as a white solid (6 g, 85%). 1H NMR (CDCl3) δ 16.4 (br s, 1 H), 11.1 (br s, 1 H), 8.19 (d,J=8 Hz, 1H), 8.05 (d,J=8 Hz, 1H), 7.84 (t,J=8, 8 Hz, 1H), 7.52 (t,J=8 Hz, 1H), 2.74 (s, 3H); ESI-MS 235.9 m/z (MH+).

後処理

  1. temperatureAfter cooling
  2. filtrationThe resulting solid was collected via filtration
  3. washwashed with water (100 mL) and MeOH (100 mL)

出典と根拠

ORDレコード
ord-95d4e1a885bc4a8398aaf6f0e62e9cc2
出典データセット
uspto-grants-2012_01
特許番号
US08101767B2

反応ノート

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