Diethyl Carbonate → Ethyl 7-benzoyloxindole-3-carboxylate

HRID 1788955Notes

Reaction equation

HRID 1788955 reaction equation
[H-].[Na+].[C:3]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[NH:18][C:17](=[O:20])[CH2:16]2)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:21](=O)([O:25]CC)[O:22][CH2:23][CH3:24]>CN(C)C=O>[C:3]([C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:19]=1[NH:18][C:17](=[O:20])[CH:16]2[C:21]([O:22][CH2:23][CH3:24])=[O:25])(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 1709837-Benzoyl-2-oxindole

Product 1

HCID 13770526Ethyl 7-benzoyloxindole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a slurry of 365 mg. of sodium hydride in 8 ml. of dimethylformamide at 0° C. was gradually added 1.0 g. (4.22 mmoles) of 7-benzoyloxindole, and the mixture allowed to stir for 10 minutes in an ice bath. Diethyl carbonate (1.53 g., 12.7 mmoles) was added and the reaction mixture allowed to stir at ice bath temperatures for 3 hours. The mixture was then poured into 200 ml. of ice and water and the resulting precipitate filtered, washed with water and vacuum dried, 940 mg. The crude product was slurried in diethyl ether, filtered and the filtrate extracted with 0.1N aqueous sodium hydroxide solution. The base layer was separated and acidified with hydrochloric acid. The resulting precipitate was filtered and dried, 109 mg., m.p. 134° C. (dec.).

Workup

  1. customat 0° C.
  2. stirringto stir at ice bath temperatures for 3 hours
  3. additionThe mixture was then poured into 200 ml
  4. filtrationof ice and water and the resulting precipitate filtered
  5. washwashed with water and vacuum
  6. customdried
  7. filtrationfiltered
  8. extractionthe filtrate extracted with 0.1N aqueous sodium hydroxide solution
  9. customThe base layer was separated
  10. filtrationThe resulting precipitate was filtered
  11. customdried

Sources & evidence

ORD record
ord-1f33ee33022f4f018069c6a43e80935c
Source dataset
uspto-grants-1987_08
Patent number
US04686224

Reaction notes

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