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

HRID 1756578

Reaction equation

HRID 1756578 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-611836b7ee754d79b36c836e3becbecb
Source dataset
uspto-grants-1995_08
Patent number
US05441955

Linked notes

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