Ethyl formate → HCID 178486553, compound

HRID 47068

Reaction equation

HRID 47068 reaction equation
[Na].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][C:8](=[O:15])[CH2:7]2.[CH:16](OCC)=[O:17]>C(O)C>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][C:8](=[O:15])[C:7]2=[CH:16][OH:17]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 2229935,6-Dimethoxyindolin-2-oneHCID 5360545Sodium

Product 1

HCID 178486553HCID 178486553, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a warm solution of 1.5 g. sodium in 35 ml. ethanol was added 10 g. of 5,6-dimethoxy oxindole [J. Am. Chem. Soc. 77 3844 (1955)]. Then 30 ml. ethyl formate was added. A solid formed. The mixture was stirred and heated 10 minutes. A stream of nitrogen was blown over the mixture to evaporate as much solvent as possible. Then a solution of 6.5 ml. concentrated hydrochloric acid and 50 ml. water was added. The resulting clear solution was concentrated in vacuum and the resulting solid filtered and washed with ice water. Yield: 10.55 g., m.p. 216°-217° C.

Workup

  1. customA solid formed
  2. temperatureheated 10 minutes
  3. customto evaporate as much solvent as possible
  4. additionwater was added
  5. concentrationThe resulting clear solution was concentrated in vacuum
  6. filtrationthe resulting solid filtered
  7. washwashed with ice water

Sources & evidence

ORD record
ord-eb5a423b340c4000879925cde7a6170a
Source dataset
uspto-grants-1979_11
Patent number
US04176191

Linked notes

Loading…