Sodium Acetate → HCID 20303921, compound

HRID 1732590Notes

Reaction equation

HRID 1732590 reaction equation
C([C:4]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]2[C:5]=1[C:6]([CH2:14][CH2:15][C:16]([OH:18])=O)=[CH:7][NH:8]2)(O)=O.C([O-])(=O)C.[Na+]>C(OC(=O)C)(=O)C>[Cl:13][C:10]1[C:9]2[NH:8][CH:7]=[C:6]3[CH2:14][CH2:15][C:16](=[O:18])[C:4]([C:5]=23)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 20303928HCID 20303928, compound

Product 1

HCID 20303921HCID 20303921, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 4-carboxy-7-chlorindole-3-propionic acid (40 g, 0.15 mole), acetic anhydride (320 ml), and anhydrous sodium acetate (3.0 g) is stirred and heated at reflux for 18 hours in the dark. The reaction mixture is cooled and then the solvent is removed under vacuum. The residue is taken up in ethanol (180 ml) and sodium hydroxide 10% (155 ml) is added slowly keeping the temperature below 45° C. After stirring for 1 hour at ambient temperature most of the ethanol is removed in vacuo and the solid that separates is recovered by filtration and dried. The yield of 8-chloro-3,4-dihydrobenz[cd]-indol-5(1H)-one is 9.1 g (30%) melting 175°-180° C. (dec). The pure compound, is crystalized from toluene and melts 185°-187° C. (dec.). ##STR14##

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 hours in the dark
  3. temperatureThe reaction mixture is cooled
  4. customthe solvent is removed under vacuum
  5. additionsodium hydroxide 10% (155 ml) is added slowly
  6. customthe temperature below 45° C
  7. stirringAfter stirring for 1 hour at ambient temperature most of the ethanol
  8. customis removed in vacuo
  9. filtrationthe solid that separates is recovered by filtration
  10. customdried
  11. customThe pure compound, is crystalized from toluene

Sources & evidence

ORD record
ord-428f0d3991b64a1b85de5e6d32f651e0
Source dataset
uspto-grants-1980_12
Patent number
US04238486

Reaction notes

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