Dichloromethane → HCID 178454480, compound

HRID 1168837Notes

Reaction equation

HRID 1168837 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]([O:20][CH3:21])[CH:13]=2.C(N(CC)CC)C.ClCCl>CN(C)C=O>[OH:19][C:18]1[C:17]2[C:12](=[CH:13][C:14]([O:20][CH3:21])=[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 6344DichloromethaneHCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 178487723HCID 178487723, compound

Product 1

HCID 178454480HCID 178454480, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Butyryl chloride (0.63 mL, 6.1 mmol) was added dropwise to a solution containing 3-amino-7-methoxyquinolin-4-ol hydrochloride (1.0 g, 5.26 mmol), triethylamine (2.35 mL, 16.8 mmol), dichloromethane (30 mL) and N,N-dimethylformamide (10 mL). The reaction mixture was maintained at ambient temperature overnight. The N,N-dimethylformamide was removed under vacuum and the resulting solid was partitioned between dichloromethane (100 mL) and water (100 mL). The organic fraction was washed with water, dried over magnesium sulfate, filtered and then concentrated under vacuum to provide 0.86 g of N-(4-hydroxy-7-methoxyquinolin-3-yl)butanamide as a tan solid.

Workup

  1. customThe N,N-dimethylformamide was removed under vacuum
  2. customthe resulting solid was partitioned between dichloromethane (100 mL) and water (100 mL)
  3. washThe organic fraction was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0844315bb2f54feeb92d85799f9a780e
Source dataset
uspto-grants-2003_09
Patent number
US06627640B2

Reaction notes

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