Dimethylformamide → 2-hydroxy-1H-quinolin-4-one

HRID 1902362Notes

Reaction equation

HRID 1902362 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=[O:12])[O:4][C:2]2=O.[C:13](CC(OC)=O)#N.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[OH:12][C:5]1[CH:13]=[C:2]([OH:4])[C:1]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7747Methyl cyanoacetateHCID 8359Isatoic AnhydrideHCID 11430Potassium Carbonate

Product 1

HCID 1785165532-hydroxy-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

A 200 ml three neck flask, equipped as described previously was charged with 16.3 g isatoic anhydride, 9.9 g methyl cyanoacetate, 8.3 g anhydrous potassium carbonate (molecular weight 138.2), and 16 g DMF. The reaction mixture was agitated at 28° to 30° C. for 1 hr. There was a slow evolution of gas during this period. The temperature was then gradually raised to 90° C. over a period of 90 minutes and kept at 90° C. for an additional 15 minutes. The gas evolution, which became strong and steady at the elevated temperature, gradually came to a stop at the end of the heating period. The reaction mixture, while still hot, was then dissolved in a charge of 60 ml of water and transferred into a 300 ml autoclave; an additional 20 ml portion of water was used to wash the flask. A 12 g charge of sodium hydroxide (molecular weight 40) pellets was added: the autoclave was closed, and heated at 135° to 140° C. with constant agitation for four hours. The desired product was isolated as described in Example 1. The yield was 12.93 g pure 2,4-dihydroxyquinoline (m.p. 353°-355° C.), 80.23 percent of theory based on isatoic anhydride.

Workup

  1. waitkept at 90° C. for an additional 15 minutes
  2. dissolutionThe reaction mixture, while still hot, was then dissolved in
  3. washto wash the flask
  4. additionA 12 g charge of sodium hydroxide (molecular weight 40) pellets
  5. additionwas added
  6. customthe autoclave was closed
  7. temperatureheated at 135° to 140° C. with constant agitation for four hours

Sources & evidence

ORD record
ord-620d20a55ff84d89a32a12a06f2a540b
Source dataset
uspto-grants-1982_12
Patent number
US04362876

Reaction notes

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