Sulfuric Acid → 2-hydroxyimino-N-(6-quinolinyl)acetamide

HRID 1264007Notes

Reaction equation

HRID 1264007 reaction equation
NC1C=C2C(=CC=1)N=CC=C2.[OH:12][N:13]=[CH:14][C:15]([NH:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]=[CH:23][CH:22]=[CH:21]2)=[O:16].S(=O)(=O)(O)[OH:29]>>[OH:12][N:13]=[CH:14][C:15]([NH:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[N:24]=[CH:23][CH:22]=[CH:21]2)=[O:16].[C:14]1(=[O:29])[C:19]2=[C:20]3[C:25](=[CH:26][CH:27]=[C:18]2[NH:17][C:15]1=[O:16])[N:24]=[CH:23][CH:22]=[CH:21]3

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 113736-AminoquinolineHCID 734148442-hydroxyimino-N-(6-quinolinyl)acetamide

Product 2

HCID 213070621H-Pyrrolo[3,2-f]quinoline-1,2(3H)-dioneYield 31%HCID 734148442-hydroxyimino-N-(6-quinolinyl)acetamideYield 61%

Procedure

2-Hydroxyimino-N-quinolin-6-yl-acetamide was prepared in 61% yield from 6-aminoquinoline according to Procedure A: 1H NMR (DMSO-d6): δ 12.4 (s, 1H), 10.8 (s, 1H), 9.0 (d, 1H), 8.8 (d, 1H), 8.7 (s, 1H), 8.2 (s, 2H), 7.81 (m, 1H), 7.78 (s, 1H); C11H9N3O2: APCI−MS m/z 216 (M+H)+. To a 1-L 3-neck round bottom flask was placed a magnetic stir bar and 110 mL of concentrated sulfuric acid. The flask was fitted with a thermometer to monitor the temperature of the reaction. The sulfuric acid was heated to 100° C. followed by slow addition of 2-hydroxyimino-N-quinolin-6-yl-acetamide (26.0 g, 0.121 mol). Heat to the reaction was maintained for approximately 1 h. The flask was removed from the heat source, and the reaction was poured slowly and carefully onto a mixture of 1 Kg of ice and 200 g of sodium carbonate. The residual reaction mixture in the reaction vessel was washed out with an additional 40 mL of cold water. The resulting aqueous slurry was stirred for about 1 h and filtered. The solid was washed thoroughly with water, filtered, and air dried to yield 7.31 g (31%) of 3-H-pyrrolo[3,2-f]quinoline-1,2-dione: 1H NMR (DMSO-d6): δ 11.1 (s, 1H), 8.8 (d, 1H), 8.7 (d, 1H), 8.2 (d, 1H), 7.6 (m, 1H), 7.4 (d, 1H); APCI−MS m/z 197 (M−H)−. The title compound was prepared in 77% yield from 3-H-pyrrolo[3,2-f]quinoline-1,2-dione and 4-hydrazinophenylmethane sulfonamide according to Procedure G: 1H NMR (DMSO-d6): δ 13.1 (s, 1H), 11.5 (s, 1H), 9.3 (d, 1H), 8.9 (d, 1H), 8.0 (d, 1H), 7.9 (m, 1H), 7.6 (d, 1H), 7.6(d, 2H), 7.4 (d, 2H), 6.9(d, 1H), 4.3 (s, 2H), 2.55 (d, 3H); APCI−MS m/z 396 (M+H)+.

Workup

  1. customTo a 1-L 3-neck round bottom flask was placed
  2. customThe flask was fitted with a thermometer
  3. customthe temperature of the reaction
  4. temperatureHeat to the reaction
  5. temperaturewas maintained for approximately 1 h
  6. customThe flask was removed from the heat source
  7. additionthe reaction was poured slowly and carefully onto a mixture of 1 Kg of ice and 200 g of sodium carbonate
  8. customThe residual reaction mixture in the reaction vessel
  9. washwas washed out with an additional 40 mL of cold water
  10. filtrationfiltered
  11. washThe solid was washed thoroughly with water
  12. filtrationfiltered
  13. customair dried

Sources & evidence

ORD record
ord-c86623ae332149d4af98526269f3f68e
Source dataset
uspto-grants-2003_04
Patent number
US06541503B2

Reaction notes

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