8-Chloro-[1,3]dioxolo [4,5-g]quinoline-7-carboxylic acid (2-pyridin-2yl-ethyl)-amide → HCID 178418371, compound

HRID 611640

Reaction equation

HRID 611640 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][NH:9][C:10]([C:12]1[CH:13]=[N:14][C:15]2[CH:16]=[C:17]3[O:25][CH2:24][O:23][C:18]3=[CH:19][C:20]=2[C:21]=1Cl)=[O:11].[SH2:26].[Na]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][NH:9][C:10]([C:12]1[CH:13]=[N:14][C:15]2[CH:16]=[C:17]3[O:25][CH2:24][O:23][C:18]3=[CH:19][C:20]=2[C:21]=1[SH:26])=[O:11]

Participants

4

Reactant 2

HCID 571273518-Chloro-[1,3]dioxolo [4,5-g]quinoline-7-carboxylic acid (2-pyridin-2yl-ethyl)-amideHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 178418371HCID 178418371, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 10.4 g (0.025 mol) of 8-chloro-[1,3]dioxolo [4,5-g]quinoline-7-carboxylic acid (2-pyridin-2yl-ethyl)-amide in 100 mL of ethanol was added 7.2 g (0.1 mol) of sodium hydrogensulfide and the mixture was heated at reflux for 3 hours. The mixture was cooled and the solids filtered, washed with ethanol, and then with water. The filtrate was concentrated and the solids were suspended in water, collected by filtration, and recrystallized from ethanol to give 6.8 g of the title compound, mp 258-260° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperatureThe mixture was cooled
  4. filtrationthe solids filtered
  5. washwashed with ethanol
  6. concentrationThe filtrate was concentrated
  7. filtrationcollected by filtration
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-40912572d58e484faf44f92324215029
Source dataset
uspto-grants-1999_12
Patent number
US06001863

Linked notes

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