Hydrochloric Acid → 1H-Pyrrolo[3,2-f]quinoline-1,2(3H)-dione

HRID 1387406Notes

Reaction equation

HRID 1387406 reaction equation
ON=[CH:3][C:4]([NH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)=[O:5].S(=O)(=O)(O)[OH:18].O.C(=O)([O-])[O-].[Na+].[Na+].Cl>O>[C:3]1(=[O:18])[C:8]2=[C:9]3[C:14](=[CH:15][CH:16]=[C:7]2[NH:6][C:4]1=[O:5])[N:13]=[CH:12][CH:11]=[CH:10]3

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 2735133Sodium Carbonate MonohydrateHCID 734148442-hydroxyimino-N-(6-quinolinyl)acetamide

Product 1

HCID 213070621H-Pyrrolo[3,2-f]quinoline-1,2(3H)-dioneYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

2-Hydroxyimino-N-(6-quinolinyl)acetamide (7.00 g, 32.5 mmol) was combined with 70 mL of concentrated sulfuric acid with stirring and heated to a reaction temperature of 120° C. for 20 min, followed by an hour at 95° C. The reaction was allowed to cool to room temperature and was added dropwise to a mixture of 155 g (1.25 mole) of sodium carbonate monohydrate and 200 g of ice. After the addition was complete, water (600 mL) was added gradually to the mixture with stirring until all inorganic white solid was dissolved. The aqueous mixture was neutralized to pH 7 with 1 M hydrochloric acid and the product was collected by filtration. The collected solid was added to 200 mL of water and dissolved by dropwise addition of 1 M hydrochloric acid to free entrapped salts. The product was then precipitated by addition of saturated aqueous sodium bicarbonate to pH 7. The product was collected by filtration and dried under vacuum at 55° C. to give 3.89 g (60%) of 3-H-pyrrolo[3,2-f]quinoline-1,2-dione as a red-brown solid. Mass spectrum (negative ion chemical ionization): m/z=197 (30%). NMR (DMSO-d6): δ7.43 (d, 1H, J=8.8 Hz), 7.66 (dd, 1H, J=4.1, 8.4 Hz); 8.29 (d, 1H, J=8.8 Hz); 8.72 (d, 1H, J=8.4 Hz); 8.82 (d, 1H, J=3.3 Hz); 11.2 (s, 1H).

Workup

  1. waitfollowed by an hour at 95° C
  2. temperatureto cool to room temperature
  3. additionAfter the addition
  4. stirringwith stirring until all inorganic white solid
  5. dissolutionwas dissolved
  6. filtrationthe product was collected by filtration
  7. additionThe collected solid was added to 200 mL of water
  8. dissolutiondissolved by dropwise addition of 1 M hydrochloric acid
  9. customThe product was then precipitated by addition of saturated aqueous sodium bicarbonate to pH 7
  10. filtrationThe product was collected by filtration
  11. customdried under vacuum at 55° C.

Sources & evidence

ORD record
ord-fa2018940ce84c5f94a4808733286dd5
Source dataset
uspto-grants-2001_07
Patent number
US06268391B1

Reaction notes

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