Sodium Azide → 1-Acetyl-5-(2-azidopropyl)indoline-7-carbonitrile

HRID 273845Notes

Reaction equation

HRID 273845 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:15][CH:16](Br)[CH3:17])=[CH:10][C:11]=2[C:13]#[N:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[N-:19]=[N+:20]=[N-:21].[Na+]>C(OCCOCCO)C.O>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:15][CH:16]([N:19]=[N+:20]=[N-:21])[CH3:17])=[CH:10][C:11]=2[C:13]#[N:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 200943711-Acetyl-5-(2-bromopropyl)indoline-7-carbonitrile

Product 1

HCID 200943521-Acetyl-5-(2-azidopropyl)indoline-7-carbonitrileYield 88.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8146Diethylene Glycol Monoethyl EtherSolvent

Procedure

1-Acetyl-5-(2-bromopropyl)indoline-7-carbonitrile (1.42 g) and sodium azide (0.30 g) were dissolved in diethylene glycol monoethyl ether (1.4 ml) and water (3.2 ml), and the mixture was stirred at 90° C. for 9.5 hours.-To the reaction mixture was added water, and the mixture was extracted with methylene chloride. The extract was washed with water, dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of ethyl acetate and hexane (3/1) as eluent to give 1.10 g of 1-acetyl-5-(2-azidopropyl)indoline-7-carbonitrile as an oil.

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by medium pressure liquid column chromatography on silica gel using
  6. additiona mixture of ethyl acetate and hexane (3/1) as eluent

Sources & evidence

ORD record
ord-4d202211b4c5459ba3d9cbb3607b8369
Source dataset
uspto-grants-1995_02
Patent number
US05387603

Reaction notes

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