Triethylamine → HCID 178454478, compound

HRID 1168819Notes

Reaction equation

HRID 1168819 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1[OH:20])=[CH:17][CH:16]=[C:15]([F:21])[CH:14]=2.[C:22](Cl)(=[O:26])[CH2:23][CH2:24][CH3:25].C(=O)(O)[O-].[Na+]>O1CCCC1>[F:21][C:15]1[CH:14]=[C:13]2[C:18]([C:19]([OH:20])=[C:10]([NH:9][C:22](=[O:26])[CH2:23][CH2:24][CH3:25])[CH:11]=[N:12]2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 516892Sodium BicarbonateHCID 178479097HCID 178479097, compound

Product 1

HCID 178454478HCID 178454478, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, triethylamine (6.4 mL, 46.2 mmol) was added to a suspension of 3-amino-7-fluoro-4-quinolinol hydrochloride (3 g, 14.0 mmol) in tetrahydrofuran (50 mL). Butyryl chloride (1.6 mL, 15.4 mmol) was added dropwise at ambient temperature. The reaction mixture was stirred at ambient temperature for 4 hours. Aqueous sodium bicarbonate was added and the reaction mixture was allowed to stir at ambient temperature for about 1 hour. The resulting biphasic mixture was filtered to remove solids. The solids were rinsed with diethyl ether to provide a slightly pink powder. The tetrahydrofuran layer was concentrated under vacuum to provide a dark pink solid. This solid was triturated with ether and then oven dried. The solids were combined to provide 3.0 g of N-(7-fluoro4-hydroxyquinolin-3-yl)butanamide. A 300 mg portion was recrystallized from ethyl acetate/ethanol to provide a light gray fluffy solid, m.p. 306-308° C. Analysis: Calculated for C13H13FN2O2: %C, 62.90; %H, 5.28; %N, 11.28; Found: %C, 62.95; %H, 5.34; %N, 11.14.

Workup

  1. stirringto stir at ambient temperature for about 1 hour
  2. filtrationThe resulting biphasic mixture was filtered
  3. customto remove solids
  4. washThe solids were rinsed with diethyl ether
  5. customto provide a slightly pink powder
  6. concentrationThe tetrahydrofuran layer was concentrated under vacuum
  7. customto provide a dark pink solid
  8. customThis solid was triturated with ether
  9. customoven dried

Sources & evidence

ORD record
ord-a29f67a4c4b841f8af851231401c7fef
Source dataset
uspto-grants-2003_09
Patent number
US06627640B2

Reaction notes

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