Ethanol → HCID 178486927, compound

HRID 2239519Notes

Reaction equation

HRID 2239519 reaction equation
N[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:13][CH3:14])=[C:9]([Br:12])[CH:10]=2)[N:5]=[N:4][C:3]=1[C:15](N)=[O:16].C(O)C.[OH-:21].[K+].[OH2:23]>>[Br:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:13][CH3:14])[N:5]=[N:4][C:3]([C:15]([OH:16])=[O:21])=[C:2]2[OH:23]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 67083770HCID 67083770, compound

Product 1

HCID 178486927HCID 178486927, compound

Conditions

Temperature
75 °C

Procedure

A 1 L flask was charged with 4-amino-6-bromo-7-methoxycinnoline-3-carboxamide (Method 15) (30 g, 101 mmol) and ethanol (650 ml). A suspension of potassium hydroxide (100 g, 1782 mmol) in water (350 ml) was added to the reaction and the mixture was stirred at reflux for 9 days. The reaction was then cooled and filtered through a pad of Celite which was washed with water (˜250 mL). The resulting filtrate was conc. in vacuo to remove the ethanol and the resulting aqueous solution was acidified with conc. HCl to pH 3. A precipitate formed which was collected by vacuum filtration. The resulting solid was suspended in 1.4 L of ethanol, heated to 75° C. for 15 minutes, and cooled to room temperature which provided the crude precipitate which was collected by vacuum filtration. The filter cake was washed with ethanol (˜200 mL) and diethyl ether (˜200 mL) to yield the title compound as a brown solid which was used without further purification (26.0 g, 86%). 1HNMR: 14.60 (m, br, 2H), 8.35 (s, 1H), 7.23 (s, 1H), 4.08 (s, 3H); m/z: 310.

Workup

  1. additionwas added to the reaction
  2. temperatureat reflux for 9 days
  3. temperatureThe reaction was then cooled
  4. filtrationfiltered through a pad of Celite which
  5. washwas washed with water (˜250 mL)
  6. customto remove the ethanol
  7. customA precipitate formed which
  8. filtrationwas collected by vacuum filtration
  9. temperaturecooled to room temperature which
  10. customprovided the crude precipitate which
  11. filtrationwas collected by vacuum filtration
  12. washThe filter cake was washed with ethanol (˜200 mL) and diethyl ether (˜200 mL)

Sources & evidence

ORD record
ord-33245ac8c8874ab1bb1b458283ea7a97
Source dataset
uspto-grants-2010_05
Patent number
US07723337B2

Reaction notes

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