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

HRID 1756578

반응식

HRID 1756578 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6212Chloroform용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-611836b7ee754d79b36c836e3becbecb
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05441955

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