Triethylamine → HCID 178454476, compound

HRID 1838851Notes

Reaction equation

HRID 1838851 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-5818ce4c5f224b4bb75b7ca69a7bd742
Source dataset
uspto-grants-2004_01
Patent number
US06677334B2

Reaction notes

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