Hydrochloric Acid → HCID 13195286, compound

HRID 2397557Notes

Reaction equation

HRID 2397557 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:16])[NH:10]2)=[O:4].[CH:17]([NH2:20])([CH3:19])[CH3:18].Cl>C(O)(C)C>[CH:17]([NH:20][CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9](=[O:16])[NH:10]2)=[O:4])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6363IsopropylamineHCID 132602995-(Chloroacetyl)-8-hydroxy-2(1H)-quinolinone

Product 1

HCID 13195286HCID 13195286, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

12.6 g of the 5-chloroacetyl-8-hydroxycarbostyril (IV) obtained in Example 4 or 8 was suspended in 130 ml of isopropanol, and 2515 g of isopropylamine (III) was added dropwise to the resulting suspension while stirring. The reaction mixture was then stirred at 55° to 60° C. for 3 hours. After cooling, concentrated hydrochloric acid was added to the mixture to adjust the mixture to a pH of 2 to 3, and the precipitated crystals were filtered, washed with acetone and recrystallized from methanol-dimethylformamide (1:1 by volume) to obtain 6.5 g of 5-isopropylaminoacetyl-8-hydroxycarbostyril (II) hydrochloride having a melting point of 286° - 288° C. (with decomposition as pale yellow crystals.

Workup

  1. stirringThe reaction mixture was then stirred at 55° to 60° C. for 3 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with acetone
  5. customrecrystallized from methanol-dimethylformamide (1:1 by volume)

Sources & evidence

ORD record
ord-a971ff41740b47a6a320e6aff2a92d76
Source dataset
uspto-grants-1977_05
Patent number
US04022776

Reaction notes

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