Hydrochloric Acid → HCID 18973115, compound

HRID 2394344Notes

Reaction equation

HRID 2394344 reaction equation
[Na].[Cl:2][C:3]1[N:4]=[C:5]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[CH2:6]2.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:19](OCC)=[O:20].Cl>C(O)C>[Cl:2][C:3]1[N:4]=[C:5]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[CH:6]2[C:19](=[O:20])[C:15]1[S:14][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76052Ethyl 2-thenoateHCID 5360545Sodium2×HCID 106319655,6-dichloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one

Product 1

HCID 18973115HCID 18973115, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Pellets of sodium metal (0.29 g, 12.6 mmol) were added to dry ethanol (10 mL) in a dry round-bottomed flask. When dissolution of the sodium was complete, solid 5,6-dichloro-4-azaoxindole (500 mg, 2.46 mmol) was added followed by ethyl 2-thiophenecarboxylate (0.67 mL. 5.0 mmol). The mixture was heated at reflux for one day under nitrogen. The mixture was cooled, poured into ice/water and acidified to pH 3 with 6N HCl solution. The title compound was collected by filtration and dried in vacuo to afford 607 mg (79%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for one day under nitrogen
  3. temperatureThe mixture was cooled
  4. filtrationThe title compound was collected by filtration
  5. customdried in vacuo
  6. customto afford 607 mg (79%)

Sources & evidence

ORD record
ord-d80c76be3b7a48ceae34b7587457225c
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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