Hydrochloric Acid → 3,5-Diamino-8-chloro-2,3-dihydro-quinoline-4-one

HRID 355967Notes

Reaction equation

HRID 355967 reaction equation
Cl.C([N:5]1[C:14]2[C:9](=[C:10]([NH:16]C(=O)C)[CH:11]=[CH:12][C:13]=2[Cl:15])[C:8](=[O:20])[CH:7]([NH:21]C(=O)C)[CH2:6]1)(=O)C.[OH-].[Na+]>C(Cl)(Cl)Cl>[NH2:21][CH:7]1[C:8](=[O:20])[C:9]2[C:14](=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[NH2:16])[NH:5][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 224495101-Acetyl-3,5-diacetylamino-8-chloro-2,3-dihydro-quinoline-4-one

Product 1

HCID 224495153,5-Diamino-8-chloro-2,3-dihydro-quinoline-4-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
110 °C

Procedure

8 ml of 6N hydrochloric acid was added to 514 mg of the compound prepared in (2) above, and the mixture was heated at 110° C. for 1.5 hours while stirring. After cooling chloroform was added to it, followed by the addition of 50 ml of 1N aqueous solution of sodium hydroxide while stirring. The chloroform layer was extracted, the extract was washed with saturated brine and dried over anhydrous sodium sulfate. The product was concentrated to produce 260 mg of the title compound.

Workup

  1. additionwas added to it
  2. stirringwhile stirring
  3. extractionThe chloroform layer was extracted
  4. washthe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe product was concentrated

Sources & evidence

ORD record
ord-366694c31d8848099faec75b393412af
Source dataset
uspto-grants-1998_11
Patent number
US05834476

Reaction notes

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