Hydrochloric Acid → HCID 54682853, compound

HRID 1033487Notes

Reaction equation

HRID 1033487 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]=1[C:13]([OH:15])=O.[CH3:16][NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>C1(C)C=CC=CC=1>[CH3:16][N:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:13]([C:3]1[C:4](=[O:12])[NH:5][C:6]2[C:11]([C:2]=1[OH:1])=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7515N-MethylanilineHCID 546974994-Hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

Product 1

HCID 54682853HCID 54682853, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N,N-dicyklohexylcarbodiimide (2.2 parts) is added to a mixture consisting of 1,2-dihydro-4-hydroxy-2-oxo-quinoline-3-carboxylic acid (2.0 parts), N-metylaniline (1.1 parts) and dry toluene (25 parts) while stirring. The stirring is continued at 110° C. for 4 hrs. The reaction mixture is cooled to room temperature and the precipitate formed is filtered off. The precipitate is dissolved at pH 8.2 in 2M sodium hydroxide solution and clarified by filtration to remove the N,N-dicyklohexylurea formed. The solution is acidified with hydrochloric acid solution and the precipitate formed is filtered off. The precipitate is washed with water and methanol and dried to give N-methyl-N-phenyl-1,2-dihydro-4-hydroxy-2-oxo-quinoline-3-carboxamide, m p>300° C. (1:1).

Workup

  1. additionN,N-dicyklohexylcarbodiimide (2.2 parts) is added to a mixture
  2. customthe precipitate formed
  3. filtrationis filtered off
  4. dissolutionThe precipitate is dissolved at pH 8.2 in 2M sodium hydroxide solution
  5. filtrationclarified by filtration
  6. customto remove the N,N-dicyklohexylurea
  7. customformed
  8. customthe precipitate formed
  9. filtrationis filtered off
  10. washThe precipitate is washed with water and methanol
  11. customdried

Sources & evidence

ORD record
ord-259dd2f4301c4cdcb688b66ac3b753d3
Source dataset
uspto-grants-1994_05
Patent number
US05310913

Reaction notes

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