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Dichloromethane → 3-((2-Nitro-9H-fluoren-9-ylidene)methyl)pyridin-2(1H)-one

HRID 578077
ノート
印刷プレビュー

反応式

HRID 578077 の反応式
[N+:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1)([O-:3])=[O:2].[O:17]=[C:18]1[C:23]([CH:24]=O)=[CH:22][CH:21]=[CH:20][NH:19]1.C(Cl)Cl>CO>[N+:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[CH:24][C:23]3[C:18](=[O:17])[NH:19][CH:20]=[CH:21][CH:22]=3)[C:6]=2[CH:5]=1)([O-:3])=[O:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 118312-NitrofluoreneHCID 70621962-Oxo-1,2-dihydropyridine-3-carbaldehyde

生成物 1

HCID 712719243-((2-Nitro-9H-fluoren-9-ylidene)methyl)pyridin-2(1H)-one

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
85 °C

実験手順

To a solution of 2-nitrofluorene (326 mg, 1.54 mmol) and 2-oxo-1,2-dihydro-pyridine-3-carbaldehyde (19 mg, 1.54 mmol) in 10 mL of methanol was added KF—Al2O3 (224 mg, 1.38 mmol). The resulting mixture was stirred at 85° C. After 24 hrs, TLC indicated that a new product was produced and lots of starting material was still remained. 40 mL of CH2Cl2 was added into the reaction mixture. The insoluble solid was filtrated, and the filtrate was concentrated under vacuum to give a yellow solid, which was purified by silica gel column; eluting with 60% EtOAc in hexane afforded 26 mg of CYD-1-93 as a yellow solid. 1H-NMR (600 MHz, d6-DMSO) δ 12.18 (br s, 2H), 8.77 (d, 1H, J=1.8 Hz), 8.52 (d, 1H, J=1.8 Hz), 8.28 (m, 2H), 8.15 (m, 2H), 8.10 (d, 1H, J=7.8 Hz), 8.06 (m, 2H), 7.97 (m, 2H), 7.86 (m, 2H), 7.80 (s, 1H), 7.63 (m, 1H), 7.59 (m, 1H), 7.49 (m, 3H), 7.37 (m, 1H), 6.40 (m, 2H). 13C-NMR (150 MHz, CDCl3) δ 161.2, 161.1, 146.9, 146.2, 146.1, 143.6, 142.1, 141.7, 140.5, 139.6, 138.3, 137.3, 136.1, 136.0, 133.6, 133.4, 129.3, 129.1, 129.0, 128.8, 127.9, 127.4, 126.1, 125.9, 124.0, 123.9, 123.5, 121.9, 121.5, 121.1, 120.7, 120.5, 119.0, 105.1, 105.0.

後処理

  1. customwas produced
  2. filtrationThe insoluble solid was filtrated
  3. concentrationthe filtrate was concentrated under vacuum
  4. customto give a yellow solid, which
  5. customwas purified by silica gel column
  6. washeluting with 60% EtOAc in hexane
  7. customafforded 26 mg of CYD-1-93 as a yellow solid

出典と根拠

ORDレコード
ord-1975994eb1af488eb80c3cd487091bc4
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09040567B2

反応ノート

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