Ammonia → Pyrido[3,2-g]quinoline-2,8-dicarboxylic acid

HRID 1534975Notes

Reaction equation

HRID 1534975 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([NH2:10])[C:5]([CH:6]=O)=[CH:4][C:3]=1[CH:11]=O.O=[C:14]([CH3:18])[C:15]([OH:17])=[O:16].[OH-:19].[Na+].N>O.C(O)C>[N:10]1[C:8]2[C:5](=[CH:4][C:3]3[CH:11]=[CH:18][C:14]([C:15]([OH:16])=[O:19])=[N:1][C:2]=3[CH:9]=2)[CH:6]=[CH:18][C:14]=1[C:15]([OH:17])=[O:16]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 1060Pyruvic Acid2×HCID 14798Sodium Hydroxide2×HCID 2749564HCID 2749564, compound

Product 1

HCID 13143645Pyrido[3,2-g]quinoline-2,8-dicarboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To 4,6-diaminoisophthalaldehyde (1,64 g) and 2-oxopropionic acid (1.94 g), ethyl alcohol (40 cc) was added and 2N sodium hydroxide solution (12.8 cc) was added with stirring at 80° C. and allowed to react for 4 hours. Then, 2-oxopropionic acid (0.41 g) and 2N sodium hydroxide solution (3 cc) were added and refluxed for 2 hours. After the addition of 2N aqueous ammonia (50 cc) and water (130 cc) and heating and filtration, charcoal was added with stirring. Refiltration and pH adjustment to 4-5 by 0.6N hydrochloric acid and 0.3N acetic acid a5 70°-80° C. gave solid which is hard to dissolve.

Workup

  1. customto react for 4 hours
  2. temperaturerefluxed for 2 hours
  3. temperatureheating
  4. filtrationfiltration, charcoal
  5. additionwas added
  6. stirringwith stirring
  7. customby 0.6N hydrochloric acid and 0.3N acetic acid a5 70°-80° C.
  8. customgave solid which
  9. dissolutionto dissolve

Sources & evidence

ORD record
ord-d23a80b100dc400ab055776e591cf595
Source dataset
uspto-grants-1992_02
Patent number
US05091535

Reaction notes

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