Water → HCID 22449436, compound

HRID 2257851Notes

Reaction equation

HRID 2257851 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[C:4](=[O:13])[CH2:5][CH2:6][NH:7]2.[C:14](Cl)(=[O:16])[CH3:15].O>ClCCl.N1C=CC=CC=1>[C:14]([NH:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[C:4](=[O:13])[CH2:5][CH2:6][NH:7]2)(=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 10329843HCID 10329843, compound

Product 1

HCID 22449436HCID 22449436, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

In a mixed solvent of 20 ml of dichloromethane and 1.3 ml of pyridine was dissolved 2.0 gm of 5-amino-8-methyl-2,3-dihydroquinoline-4-one. 1.2 ml of acetyl chloride was added to the solution under ice-cooling while stirring, followed by further stirring for 4 hours. After the addition of water, the reaction mixture was extracted with chloroform, washed with saturated brine, and dried over anhydrous sodium sulfate. After evaporating the solvent, the residue was crystallized in ether to obtain 1.24 gm of the title compound.

Workup

  1. temperaturecooling
  2. stirringby further stirring for 4 hours
  3. extractionthe reaction mixture was extracted with chloroform
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter evaporating the solvent
  7. customthe residue was crystallized in ether

Sources & evidence

ORD record
ord-c550d9c6933c4c68979913f60d40d372
Source dataset
uspto-grants-1997_08
Patent number
US05658920

Reaction notes

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