Triethylamine → N-[4-hydroxy-7-(trifluoromethyl)quinolin-3-yl]butanamide

HRID 1168826Notes

Reaction equation

HRID 1168826 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].Cl.[NH2:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[OH:19])=[CH:16][CH:15]=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=2.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[OH:19][C:18]1[C:17]2[C:12](=[CH:13][C:14]([C:20]([F:23])([F:21])[F:22])=[CH:15][CH:16]=2)[N:11]=[CH:10][C:9]=1[NH:8][C:1](=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 516892Sodium BicarbonateHCID 178479096HCID 178479096, compound

Product 1

HCID 178454475N-[4-hydroxy-7-(trifluoromethyl)quinolin-3-yl]butanamideYield 83.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Butyryl chloride (1.5 mL, 14.5 mmol) was added dropwise to a mixture of 3-amino-7-(trifluoromethyl)-4-quinolinol hydrochloride (3.5 g, 13.2 mmol), triethylamine (6.1 mL, 43.6 mmol) and anhydrous tetrahydrofuran (30 mL). The reaction mixture was allowed to stir for 16 hours. A small amount of aqueous sodium bicarbonate was added and the reaction mixture was stirred for 0.5 hours. The tetrahydrofuran was removed under vacuum. The resulting solid was stirred with diethyl ether, isolated by filtration, washed with water and diethyl ether, and then dried in a vacuum oven at 80° C. overnight to provide 3.3 g of N-[4-hydroxy-7-(trifluoromethyl)quinolin-3-yl]butanamide as a cream colored solid.

Workup

  1. stirringthe reaction mixture was stirred for 0.5 hours
  2. customThe tetrahydrofuran was removed under vacuum
  3. stirringThe resulting solid was stirred with diethyl ether
  4. customisolated by filtration
  5. washwashed with water and diethyl ether
  6. customdried in a vacuum oven at 80° C. overnight

Sources & evidence

ORD record
ord-285f3e11d4d2415e81c50055e7b631d1
Source dataset
uspto-grants-2003_09
Patent number
US06627640B2

Reaction notes

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