Dichloromethane → 3-Acetylamino-5-amino-8-chloro-2,3-dihydroquinoline-4-one

HRID 2257867Notes

Reaction equation

HRID 2257867 reaction equation
[NH2:1][CH:2]1[C:11](=[O:12])[C:10]2[C:5](=[C:6]([Cl:14])[CH:7]=[CH:8][C:9]=2[NH2:13])[NH:4][CH2:3]1.ClCCl.C1C[O:21][CH2:20][CH2:19]1.C(OC(=O)C)(=O)C>N1C=CC=CC=1>[C:20]([NH:1][CH:2]1[C:11](=[O:12])[C:10]2[C:5](=[C:6]([Cl:14])[CH:7]=[CH:8][C:9]=2[NH2:13])[NH:4][CH2:3]1)(=[O:21])[CH3:19]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 224495153,5-Diamino-8-chloro-2,3-dihydro-quinoline-4-one

Product 1

HCID 224495543-Acetylamino-5-amino-8-chloro-2,3-dihydroquinoline-4-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

260 mg of the compound prepared in (3) above was dissolved into a mixed solvent of 5 ml of dichloromethane and 5 ml of THF. To this solution were added 0.16 ml of pyridine and 0.13 ml of acetic anhydride while stirring under ice cooling, and the mixture was stirred for 20 minutes. The reaction product was concentrated, and after the addition of chloroform, the residue was washed with saturated sodium bicarbonate and saturated brine, and dried over anhydrous sodium sulfate. The product was concentrated and the residue was charged into ether and petroleum ether in to produce 287 mg powder of the title compound.

Workup

  1. stirringthe mixture was stirred for 20 minutes
  2. concentrationThe reaction product was concentrated
  3. additionafter the addition of chloroform
  4. washthe residue was washed with saturated sodium bicarbonate and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe product was concentrated
  7. additionthe residue was charged into ether and petroleum ether in

Sources & evidence

ORD record
ord-bb76f14a1e5942dc905d71f9b7854550
Source dataset
uspto-grants-1997_08
Patent number
US05658920

Reaction notes

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