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

HRID 401229ノート

反応式

HRID 401229 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, 1H), 11.1 (br s, 1H), 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-555753fc7dba438cb2bfee8522159992
出典データセット
uspto-grants-2014_06
特許番号
US08741925B2

反応ノート

読み込み中…