Hydrochloric Acid → 6-Chloro-3-(2-thenoyl)-4-azaoxindole

HRID 2394332Notes

Reaction equation

HRID 2394332 reaction equation
[Na].[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][C:8](=[O:12])[NH:9]2)=[N:5][CH:4]=1.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18](OCC)=[O:19].Cl>C(O)C>[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]([C:18](=[O:19])[C:14]3[S:13][CH:17]=[CH:16][CH:15]=3)[C:8](=[O:12])[NH:9]2)=[N:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76052Ethyl 2-thenoateHCID 5360545Sodium2×HCID 104873236-Chloro-1,3-dihydropyrrolo[3,2-B]pyridin-2-one

Product 1

HCID 189730556-Chloro-3-(2-thenoyl)-4-azaoxindole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Pellets of sodium metal (3.4 g, 0.15 mmol) were added to dry ethanol (90 mL) in a dry round-bottomed flask. When dissolution of the sodium was complete, solid 6-chloro-4-azaoxindole (5.0 g 29.7 mmol) was added followed by ethyl 2-thiophenecarboxylate (8 mL, 55 mmol). The mixture was heated under nitrogen at reflux overnight during which a precipitate formed. The mixture was cooled, poured into ice/water and acidified to pH 3 with 6N HCl solution. The solid azaoxindole (7.8 g, 94%) (m.p. 250°) was collected by filtration washing with water and ether and dried in vacuo with heating.

Workup

  1. temperatureThe mixture was heated under nitrogen
  2. temperatureat reflux overnight during which a precipitate
  3. customformed
  4. temperatureThe mixture was cooled
  5. filtrationThe solid azaoxindole (7.8 g, 94%) (m.p. 250°) was collected by filtration
  6. washwashing with water and ether
  7. customdried in vacuo
  8. temperaturewith heating

Sources & evidence

ORD record
ord-6b17b4e712584f158b7c34048411e2a1
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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