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

HRID 1708337Notes

Reaction equation

HRID 1708337 reaction equation
[Na+].[Cl:2][C:3]1[CH:4]=[CH:5]C(C(O)=O)=[C:7]([NH:9][CH2:10]C([O-])=O)[CH:8]=1.[C:17]([O:20][C:21](=O)[CH3:22])(=[O:19])[CH3:18].[C:24]([O-:27])(=O)[CH3:25].[Na+].C(=O)=O>>[CH3:25][C:24]([N:9]1[C:7]2[CH:8]=[C:3]([Cl:2])[CH:4]=[CH:5][C:22]=2[C:21]([O:20][C:17]([CH3:18])=[O:19])=[CH:10]1)=[O:27]

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 L, 3-neck flask equipped with mechanical stirring, reflux condenser and gas evolution bubbler was placed 335 g (1.33M) of 5-chloro-2-carboxyphenylglycine sodium salt, 2.3 l acetic anhydride and 421 g of anhydrous sodium acetate. The mixture was brought to reflux and maintained for 3 hours until the evolution of carbon dioxide was nearly complete. The mixture was placed in a beaker while hot and chilled to 0° C. overnight. The next day, the product was filtered off and mixed with 2 L water and stirred for 1 hour to hydrolyze any residual acetic anhydride. The solid was filtered off and washed with water and then dried in vacuo. This crude material, when dry, was 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 150 g and had a melting point of 112°-113° C.

Workup

  1. customInto a 5 L, 3-neck flask equipped with mechanical stirring
  2. temperaturereflux condenser
  3. temperatureto reflux
  4. filtrationThe next day, the product was filtered off
  5. additionmixed with 2 L water
  6. filtrationThe solid was filtered off
  7. washwashed with water
  8. customdried in vacuo
  9. dry with materialThis crude material, when dry
  10. dissolutionwas dissolved in the minimum of hot ethyl acetate
  11. customto crystallize overnight at 0° C
  12. filtrationAfter filtering
  13. washwashing with a little cold hexane
  14. customdrying in vacuo

Sources & evidence

ORD record
ord-393e7add936a401ab7b885e86fdeefde
Source dataset
uspto-grants-1994_10
Patent number
US05358854

Reaction notes

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