Toluene → HCID 69640155、化合物

HRID 2188231ノート

反応式

HRID 2188231 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7](=O)[C:8]3[C:13]([NH:14][C:15]=2[CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1(C)C=CC=CC=1.[OH-].[Na+]>C(OCC)C.C(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C:8]3[C:13]([NH:14][C:15]=2[CH:16]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

参加物

8

反応物 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 64542543-Methoxyacridin-9-oneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 69640155HCID 69640155、化合物収率 98%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 15.29 g of 3-methoxyacridone (67.9 mmol) in 200 mL of diethyl ether was added 7.73 g of LiAlH4 slowly portionwise. Once evolution of H2 ceased, 200 mL of dry toluene was added under inert atmosphere and the reaction was stirred at reflux for 2 h. The reaction mixture was cooled to 0° C. and dropwise addition of 8.0 mL of water, 8.0 mL of 15% NaOH (aq) and 24.0 mL of water were performed sequentially. 500 mL of CH2Cl2 was added and the resultant precipitate was filtered, washed with 500 mL of CH2Cl2 and discarded. The filtrate was concentrated in vacuo, resuspended in hexanes, and again concentrated to afford 14.06 g of 3-methoxyacridan (98%).

後処理

  1. temperatureat reflux for 2 h
  2. filtrationthe resultant precipitate was filtered
  3. washwashed with 500 mL of CH2Cl2
  4. concentrationThe filtrate was concentrated in vacuo
  5. concentrationagain concentrated

出典と根拠

ORDレコード
ord-a42fb745cc114cd9bd1d48021690e9cb
出典データセット
uspto-grants-2002_06
特許番号
US06410732B2

反応ノート

読み込み中…