Dimethylformamide → 5-Chloro-3-methyl-2-oxo-3H-oxazolo[4,5-h]quinoline

HRID 1284497Notes

Reaction equation

HRID 1284497 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([NH2:12])[C:9]([OH:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[H-].[Na+].CN([CH:19]=[O:20])C.[CH3:21]I>O>[Cl:1][C:2]1[C:3]2[CH:4]=[CH:5][CH:6]=[N:7][C:8]=2[C:9]2[O:13][C:19](=[O:20])[N:12]([CH3:21])[C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 4174907-Amino-5-chloroquinolin-8-ol

Product 1

HCID 135379905-Chloro-3-methyl-2-oxo-3H-oxazolo[4,5-h]quinolineYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5-Chloro-7-amino-8-hydroxyquinoline (3.0 g, 13.6 mmol), degreased sodium hydride (1.0 g, 50% in oil) and DMF at 60° C. was added methyl iodide. The reaction was stirred for 1 hour. Water was added and the mixture was extracted with chloroform (3×). The organic extracts were combined and concentrated. The remaining solid was crystallized from ethanol to give 1.4 g (45% yield) of product. M.P. 219°-221° C.

Workup

  1. extractionthe mixture was extracted with chloroform (3×)
  2. concentrationconcentrated
  3. customThe remaining solid was crystallized from ethanol

Sources & evidence

ORD record
ord-db6079d8bda6421993c6f6ca6f948c3a
Source dataset
uspto-grants-1986_01
Patent number
US04563463

Reaction notes

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