Sodium Azide → 2-Azido-1-(3-phenyl-2,3-dihydro-1H-indol-1-yl)ethan-1-one

HRID 262298Notes

Reaction equation

HRID 262298 reaction equation
Cl[CH2:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6]1)=[O:4].[N-:20]=[N+:21]=[N-:22].[Na+]>C(O)C.O>[N:20]([CH2:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6]1)=[O:4])=[N+:21]=[N-:22]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 213204582-Chloro-1-(3-phenyl-2,3-dihydro-1H-indol-1-yl)ethan-1-one

Product 1

HCID 213204672-Azido-1-(3-phenyl-2,3-dihydro-1H-indol-1-yl)ethan-1-oneYield 68.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 4.0 g of N-chloroacetyl-3-phenylindoline and 1.1 g of sodium azide in 70 ml of 80% aqueous ethanol was refluxed for one hour. After cooling, the solution was diluted with 100 ml of water and extracted with methylene chloride. Evaporation of the solvent gave 2.8 g of the desired N-azidoacetyl-3-phenylindoline having a melting point of 72°-3° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with methylene chloride
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-142485ee04114278a3b866ddd7468203
Source dataset
uspto-grants-1979_05
Patent number
US04153789

Reaction notes

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