Hydrochloric Acid → HCID 13533222, compound

HRID 2397559Notes

Reaction equation

HRID 2397559 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]([NH2:21])([CH2:19][CH3:20])[CH3:18].Cl>C(O)C>[CH:17]([NH:21][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])([CH2:19][CH3:20])[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24874Sec-ButylamineHCID 132602995-(Chloroacetyl)-8-hydroxy-2(1H)-quinolinone

Product 1

HCID 13533222HCID 13533222, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.3 g of the 5-chloroacetyl-8-hydroxycarbostyril (IV) obtained in Example 4 or 8 was suspended in 50 ml of ethanol, and 5 g of sec-butylamine was added dropwise to the resulting suspension while stirring followed by stirring at 60° to 65° C. for 5 hours. After cooling, the resulting mixture was adjusted to a pH of 3 with concentrated hydrochloric acid. The precipitated crystals were filtered, washed with acetone and recrystallized from methanol-ethanol (1:1 by volume) to obtain 2.9 g of 5-sec-butylaminoacetyl-8-hydroxycarbostyril (II) hydrochloride having a melting point of 289° - 291° C. (with decomposition) as pale yellow crystals.

Workup

  1. stirringby stirring at 60° to 65° C. for 5 hours
  2. temperatureAfter cooling
  3. filtrationThe precipitated crystals were filtered
  4. washwashed with acetone
  5. customrecrystallized from methanol-ethanol (1:1 by volume)

Sources & evidence

ORD record
ord-695ada1b575647afa7b62f564299d6ad
Source dataset
uspto-grants-1977_05
Patent number
US04022776

Reaction notes

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