Hydrochloric Acid → 10-Fluoroindolo[2,1-b]quinazoline-6,12-dione

HRID 215795

反応式

HRID 215795 の反応式
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=O)[C:7]2=[O:12].[C:13]12[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH:18]C(=O)O[C:14]2=[O:15].CN(C1C=CC=CN=1)C.Cl>N1C=CC=CC=1.C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]1[C:8](=[N:18][C:19]3[C:13]([C:14]1=[O:15])=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:7]2=[O:12]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8359Isatoic AnhydrideHCID 218852-DimethylaminopyridineHCID 5864187-Fluoroisatin

生成物 1

HCID 47865210-Fluoroindolo[2,1-b]quinazoline-6,12-dione収率 14%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6212Chloroform溶媒

実験手順

A solution of 7-fluoroisatin (300 mg, 1.8 mmol), isatoic anhydride (1.2 g, 7.3 mmol), and dimethylaminopyridine (222 mg, 2 mmol) in 5 mL of pyridine were heated at reflux temperature for 64 h. 50 mL of 0.2N HCl and 100 mL of chloroform were added and the chloroform layer was separated. The water layer was extracted with chloroform and the combined organic extracts were concentrated. Chromatography on silica gel eluting with chloroform gave the title compound in 14% yield: mp 264-267° C.; 1H NMR (300 MHz, CDCl3) δ 8.46 (d, 1H) 8.02 (d, 1H) 7.82-7.92 (m, 1H) 7.79 (d, 1H) 7.64-7.74 (m, 1H) 7.52-7.64 (m, 1H) 7.40-7.49 (m, 1H).

後処理

  1. temperatureat reflux temperature for 64 h
  2. customthe chloroform layer was separated
  3. extractionThe water layer was extracted with chloroform
  4. concentrationthe combined organic extracts were concentrated

出典と根拠

ORDレコード
ord-7b161f3376b04438970a1c230d185360
出典データセット
uspto-grants-2012_06
特許番号
US08193185B2

関連ノート

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