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

HRID 1169694ノート

反応式

HRID 1169694 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-59ae8db5a5d743238efadb32a6f57287
出典データセット
uspto-grants-2010_11
特許番号
US07825131B2

反応ノート

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