Hydrochloric Acid → HCID 18688797, compound

HRID 128870Notes

Reaction equation

HRID 128870 reaction equation
ClC1C=CC=CC=1[C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH3:16])=[CH:12][C:13]=2[CH3:15])[C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[C:7]1[C:24]([O:26][CH3:27])=[O:25])=O.[OH-].[Na+].Cl>CO>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:8]1[C:9]2[C:14](=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[CH:10]=2)[N:6]([CH3:4])[C:7]=1[C:24]([O:26][CH3:27])=[O:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18688885HCID 18688885, compound

Product 1

HCID 18688797HCID 18688797, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 1-(2-chlorobenzoyl)-3-(2-chlorophenyl)-5,7-dimethylindole-2-carboxylate (compound K) was obtained in the same manner as for compounds I and J in Reference Example 4. In 20 cc of methanol was dissolved 0.96 g of compound K, followed by adding thereto 4.2 cc of 2N sodium hydroxide, and the resulting mixture was heated under reflux for 2 hours. After cooling, the mixture was acidified with 2N HCl, followed by extraction with ethyl acetate. The extract was dried over magnesium sulfate and distilled to remove the solvent. The resulting crude product was dissolved in 2 cc of dimethylformamide, and 0.26 g of 63% sodium hydride in 1.5 cc of dimethylformamide was added at room temperature. The resulting mixture was stirred at room temperature for 30 minutes, and then 0.4 cc of methyl iodide was added dropwise and stirred for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The extract was dried over magnesium sulfate and distilled to remove the solvent. The crude product thus obtained was washed with hexane to obtain 0.41 g of methyl 3-(2-chlorophenyl)-1,5,7-trimethylindole-2-carboxylate (compound L).

Workup

  1. additionby adding
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. extractionfollowed by extraction with ethyl acetate
  5. dry with materialThe extract was dried over magnesium sulfate
  6. distillationdistilled
  7. customto remove the solvent
  8. dissolutionThe resulting crude product was dissolved in 2 cc of dimethylformamide
  9. addition0.26 g of 63% sodium hydride in 1.5 cc of dimethylformamide was added at room temperature
  10. addition0.4 cc of methyl iodide was added dropwise
  11. stirringstirred for 2 hours
  12. additionWater was added to the reaction mixture
  13. extractionfollowed by extraction with ethyl acetate
  14. dry with materialThe extract was dried over magnesium sulfate
  15. distillationdistilled
  16. customto remove the solvent
  17. customThe crude product thus obtained
  18. washwas washed with hexane

Sources & evidence

ORD record
ord-fcf98931d74845888746491b9f5f4551
Source dataset
uspto-grants-1995_11
Patent number
US05464863

Reaction notes

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