Carbon Dioxide → 1-acetyl-6-chloro-1H-indol-3-yl acetate

HRID 2379671Notes

Reaction equation

HRID 2379671 reaction equation
[Na+].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:14](O)=O)=[C:7]([NH:9][CH2:10]C([O-])=O)[CH:8]=1.[C:17]([O-:20])(=[O:19])[CH3:18].[Na+].C(=O)=O.C(O[C:29](=[O:31])[CH3:30])(=O)C>>[CH3:30][C:29]([N:9]1[C:7]2[CH:8]=[C:3]([Cl:2])[CH:4]=[CH:5][C:6]=2[C:14]([O:19][C:17]([CH3:18])=[O:20])=[CH:10]1)=[O:31]

Participants

5

Reactant 4

HCID 280Carbon DioxideHCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 666849095-Chloro-2-carboxyphenylglycine sodium salt

Product 1

HCID 117015591-acetyl-6-chloro-1H-indol-3-yl acetate

Conditions

Temperature
0 °C

Procedure

Into a 5 liter, 3-neck flask equipped with mechanical stirring, reflux condenser and gas evolution bubbler is placed 335 g (1.33M) of 5-chloro-2-carboxyphenylglycine sodium salt, 2.3 liters acetic anhydride and 421 g of anhydrous sodium acetate. The mixture is brought to reflux and maintained for 3 hours until the evolution of carbon dioxide is nearly complete. The mixture is placed in a beaker while hot and chilled to 0° C. overnight. The next day the product is recovered by filtration and mixed with 2 liters water and stirred for 1 hour to hydrolyze any residual acetic anhydride. This crude material, when dry, is dissolved in the minimum of hot ethyl acetate and allowed to crystallize overnight at 0° C. After filtering and washing with a little cold hexane, and drying in vacuo, the product weighed about 150 g and has a melting point of about 112°-113° C.

Workup

  1. customInto a 5 liter, 3-neck flask equipped with mechanical stirring
  2. temperaturereflux condenser
  3. temperatureto reflux
  4. filtrationThe next day the product is recovered by filtration
  5. additionmixed with 2 liters water
  6. dry with materialThis crude material, when dry
  7. dissolutionis dissolved in the minimum of hot ethyl acetate
  8. customto crystallize overnight at 0° C
  9. filtrationAfter filtering
  10. washwashing with a little cold hexane
  11. customdrying in vacuo

Sources & evidence

ORD record
ord-23929648ef7a4164b623fd4dd408b5eb
Source dataset
uspto-grants-1994_11
Patent number
US05364767

Reaction notes

Loading…