Triethylamine → HCID 178454476, compound

HRID 1168784Notes

Reaction equation

HRID 1168784 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([Cl:19])[CH:12]=2.C(N(CC)CC)C>O1CCCC1>[Cl:19][C:13]1[CH:12]=[C:11]2[C:16]([C:17]([OH:18])=[C:8]([NH:7][C:1](=[O:5])[CH2:2][CH2:3][CH3:4])[CH:9]=[N:10]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 178507996HCID 178507996, compound

Product 1

HCID 178454476HCID 178454476, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, butyryl chloride (0.76 mL, 7.3 mmol) was added dropwise to a mixture of 3-amino-7-chloro-4-hydroxyquinoline (1.3 g, 6.7 mmol), triethylamine (3.0 mL, 21.5 mmol) and anhydrous tetrahydrofuran (20 mL). The reaction mixture was maintained at ambient temperature overnight. The resulting precipitate was isolated by filtration, washed with water followed by tetrahydrofuran, and then vacuum dried to provide 1.05 g of N-(7-chloro-4-hydroxyquinolin-3-yl)butanamide as a tan powder.

Workup

  1. customThe resulting precipitate was isolated by filtration
  2. washwashed with water
  3. customvacuum dried

Sources & evidence

ORD record
ord-5b074019c50e4beeab47595ca480d319
Source dataset
uspto-grants-2003_09
Patent number
US06627638B2

Reaction notes

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