Sodium Hydroxide → HCID 14931744, compound

HRID 1252057Notes

Reaction equation

HRID 1252057 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12](C(=O)C)[CH2:11]2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[N+:22]([O-])([O-:24])=[O:23].[K+].[OH-].[Na+]>S(=O)(=O)(O)O>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:22]([O-:24])=[O:23])[CH:17]=3)[NH:12][CH2:11]2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 14931743HCID 14931743, compound

Product 1

HCID 14931744HCID 14931744, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 3-(1-acetyl-4-piperidyl)-1acetylindoline (0.3 g) in conc. sulfuric acid (5 ml) was added potassium nitrate (0.12 g) in small portions at a temperature not exceeding 10° C. with stirring. The mixture was stirred at the same temperature for 1 hour and at ambient temperature for 7 hours. The reaction mixture was poured into ice and allowed to stand at ambient temperature for 3 days. The aqueous solution was neutralized with 2N aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off and the residue was subjected to column chromatography on silica gel, followed by elution with a mixture of chloroform and methanol to give 3-(1-acetyl-4-piperidyl)-5-nitroindoline (0.12 g).

Workup

  1. customexceeding 10° C.
  2. stirringThe mixture was stirred at the same temperature for 1 hour and at ambient temperature for 7 hours
  3. additionThe reaction mixture was poured into ice
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off
  8. washfollowed by elution with a mixture of chloroform and methanol

Sources & evidence

ORD record
ord-d4840c50c2554ef38ed81dfc11686509
Source dataset
uspto-grants-1988_05
Patent number
US04742057

Reaction notes

Loading…