Hydrochloric Acid → HCID 18973026, compound

HRID 2394336Notes

Reaction equation

HRID 2394336 reaction equation
[Na].[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][N:11]=1)[NH:8][C:7](=[O:12])[CH2:6]2.[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:4]=[C:5]2[C:9](=[CH:10][N:11]=1)[NH:8][C:7](=[O:12])[CH:6]2[C:18](=[O:19])[C:14]1[S:13][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76052Ethyl 2-thenoateHCID 5360545Sodium2×HCID 189730325-Chloro-1,3-dihydro-2H-pyrrolo[2,3-c]pyridin-2-one

Product 1

HCID 18973026HCID 18973026, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Pellets of sodium metal (232 mg, 10 mmol) were added to dry ethanol (10 mL) in a dry round-bottomed flask. When dissolution of the sodium was complete, solid 5-chloro-6-azaoxindole (340 mg, 2.0 mmol) was added followed by ethyl 2-thiophenecarboxylate (0.54 mL, 4.0 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 4 with 6N HCl solution. The solid product (475 mg) was collected by filtration, washed with water, and dried in the air. This material was recrystallized from methanol to afford the title compound (190 mg, 34%). 1H NMR (DMSO-d6): δ10.62 (br s, 1H), 8.79 (d, J=3.2 Hz, 1H), 7.92 (s, 1H), 7.77 (d, J=5 Hz, 1H), 7.65 (s, 1H), 7.17-7.14 (m, 1H).

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 product (475 mg) was collected by filtration
  6. washwashed with water
  7. customdried in the air
  8. customThis material was recrystallized from methanol

Sources & evidence

ORD record
ord-9ea4e84eadc74b05a774315ddac21b67
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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