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

HRID 215795

반응식

HRID 215795 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-7b161f3376b04438970a1c230d185360
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193185B2

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