Hydrazine → 3-Amino-1-(2,4-dimethoxybenzyl)-4-(3-fluorophenyl)-6-methoxyquinolin-2-(1H)-one

HRID 1169694노트

반응식

HRID 1169694 반응식
[Cl-].[CH3:2][O:3][C:4]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:5]=1[CH2:6][N:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)=[C:9]([N+:26]2C=CC=CC=2)[C:8]1=[O:32].NN>C(O)C>[NH2:26][C:9]1[C:8](=[O:32])[N:7]([CH2:6][C:5]2[CH:33]=[CH:34][C:35]([O:37][CH3:38])=[CH:36][C:4]=2[O:3][CH3:2])[C:16]2[C:11]([C:10]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=1)=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2

참가 물질

4

반응물 2

HCID 9321HydrazineHCID 866117061-[1-(2,4-Dimethoxybenzyl)-4-(3-fluorophenyl)-6-methoxy-2-oxo-1,2-dihydroquinolin-3-yl]pyridinium chloride

생성물 1

HCID 588522503-Amino-1-(2,4-dimethoxybenzyl)-4-(3-fluorophenyl)-6-methoxyquinolin-2-(1H)-one

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 1-[1-(2,4-dimethoxybenzyl)-4-(3-fluorophenyl)-6-methoxy-2-oxo-1,2-dihydroquinolin-3-yl]pyridinium chloride (225 mg, 0.422 mmol) and hydrazine (0.133 mL, 4.22 mmol) in 3 mL of ethanol was heated to reflux. After one hour, the reaction was cooled to room temperature. The reaction was partitioned between EtOAc and saturated NaHCO3 solution, and the organic layer dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography through SiO2 (0-5% MeOH/CH2Cl2) to provide the titled product as a white foam. 1H-NMR (500 MHz, CDCl3) δ 7.55 (m, 1H), 7.18 (d, J=8.5 Hz, 2H), 7.12 (m, 1H), 6.81 (dd, J=9.2, 2.7 Hz, 1H), 6.76 (d, J=8.5 Hz, 1H), 6.52 (br s, 1H), 6.34 (dd, J=8.5, 2.2 Hz, 1H), 5.57 (s, 2H), 3.96 (s, 3H), 3.76 (s, 3H), 3.65 (s, 3H) ppm. HRMS (ES) exact mass calculated for C25H23FN2O4 (M+H+): 435.1715. Found 435.1732.

후처리

  1. customThe reaction was partitioned between EtOAc and saturated NaHCO3 solution
  2. dry with materialthe organic layer dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash chromatography through SiO2 (0-5% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-59ae8db5a5d743238efadb32a6f57287
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825131B2

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