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

HRID 401229노트

반응식

HRID 401229 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-555753fc7dba438cb2bfee8522159992
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741925B2

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