Tert-Butylamine → HCID 13195275, compound

HRID 2397558Notes

Reaction equation

HRID 2397558 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].[C:17]([NH2:21])([CH3:20])([CH3:19])[CH3:18]>C(O)C>[C: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])([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 132602995-(Chloroacetyl)-8-hydroxy-2(1H)-quinolinone

Product 1

HCID 13195275HCID 13195275, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8.0 g of the 5-chloroacetyl-8-hydroxycarbostyril (IV) (IV) obtained Example 4 or 8 was suspended in 100 ml of ethanol, and 10 g of tert-butylamine was added dropwise to the resulting suspension while stirring followed by stirring at 55° to 60° C. for 5 hours. After the mixture was concentrated to half the volume, concentrated hydrochloric acid was added thereto to adjust the mixture to a pH of 2 to 3. The precipitated crystals were filtered, washed with acetone and recrystallized from ethanol to obtain 4.1 g of 5-tert-butylaminoacetyl-8-hydroxycarbostyril (II) having a melting point of 291° - 293° C. (with decomposition) as pale yellow crystals.

Workup

  1. stirringby stirring at 55° to 60° C. for 5 hours
  2. concentrationAfter the mixture was concentrated to half the volume, concentrated hydrochloric acid
  3. additionwas added
  4. filtrationThe precipitated crystals were filtered
  5. washwashed with acetone
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f797cf449e3646239c81d827ce9c8ef5
Source dataset
uspto-grants-1977_05
Patent number
US04022776

Reaction notes

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