Methanol → 2-Chloro-8-fluoroindolo[2,1-b]quinazoline-6,12-dione

HRID 1756563

Reaction equation

HRID 1756563 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=O)[C:7]2=[O:14].[Cl:15][C:16]1[CH:27]=[C:20]2[C:21](OC(=O)[NH:25][C:19]2=[CH:18][CH:17]=1)=[O:22].CO>CN(C=O)C.C(Cl)(Cl)Cl>[Cl:15][C:16]1[CH:27]=[C:20]2[C:19](=[CH:18][CH:17]=1)[N:25]=[C:8]1[C:7](=[O:14])[C:6]3[C:10]([N:9]1[C:21]2=[O:22])=[CH:11][CH:12]=[C:4]([F:3])[CH:5]=3

Participants

7

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 784805-Chloroisatoic anhydrideHCID 2365665-Fluoroisatin

Product 1

HCID 4785692-Chloro-8-fluoroindolo[2,1-b]quinazoline-6,12-dione

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent3×

Procedure

To a suspension of NaH (10 mmol, 40 mg 60%) in 4 mL of DMF was added 10 mmol of 5-fluoroisatin in 2 mL of DMF. After 15 min, a solution of 5-chloroisatoic anhydride in 3 mL of DMF was added. The reaction mixture was stirred for 18 h, methanol (0.5 mL) and 20 mL of chloroform was added and the organic solution was washed with water, dried (MgSO4) and concentrated to give a residue which was purified by silica gel chromatography (CHCl3 :CH3OH). Yield 77%: mp 280°-282° C.

Workup

  1. washthe organic solution was washed with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customto give a residue which
  5. customwas purified by silica gel chromatography (CHCl3 :CH3OH)

Sources & evidence

ORD record
ord-0cfebdd3820a4315bfe8dcf209410365
Source dataset
uspto-grants-1995_08
Patent number
US05441955

Linked notes

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