Water → HCID 57765303, 화합물

HRID 2061849노트

반응식

HRID 2061849 반응식
[F:1][C:2]1[CH:3]=[C:4]([I:18])[CH:5]=[C:6]2[C:11]=1[NH:10][CH:9]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]2=[O:17].C(=O)([O-])[O-].[K+].[K+].I[CH2:26][CH2:27][OH:28].O>CN(C)C=O.[Cl-].[Na+].O>[F:1][C:2]1[CH:3]=[C:4]([I:18])[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:26][CH2:27][OH:28])[CH:9]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]2=[O:17]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12225IodoethanolHCID 18753050HCID 18753050, 화합물2회

생성물 1

HCID 57765303HCID 57765303, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
90 °C

실험 절차

Ethyl 8-fluoro-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate (Intermediate 11, 7.22 g, 20 mmol) was dissolved in dimethylformamide (35 ml). Powdered potassium carbonate (8.28 g, 60 mmol) and 2-iodoethanol (11.3 ml, 145 mmol) were then added and the reaction mixture was allowed to stir at 90° C. for 1 h. The reaction mixture was cooled to room temperature and poured into brine (300 ml) then water (50 ml) was added to dissolve the material. This solution was extracted with 9:1 tetrahydrofuran:methyl tert-butyl ether (5×200 ml). The organic extracts were combined washed with brine (2×200 ml), dried over sodium sulfate, and concentrated under reduced pressure to give a dark yellow oil of ethyl 8-fluoro-1-(2-hydroxyethyl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate that was carried on to the next reaction without any further purification.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. dissolutionto dissolve the material
  3. extractionThis solution was extracted with 9:1 tetrahydrofuran
  4. washThe organic extracts were combined washed with brine (2×200 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-37205679ebeb43e598d31cc6c290f32f
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283361B2

반응 노트

불러오는 중…