Sodium Azide → 3-Azido-indan-1-one

HRID 379335

Reaction equation

HRID 379335 reaction equation
Br[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3]1.[N-:12]=[N+:13]=[N-:14].[Na+]>CN(C=O)C>[N:12]([CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3]1)=[N+:13]=[N-:14]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 117459123-Bromo-1-indanone

Product 1

HCID 216985633-Azido-indan-1-oneYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 3-Bromo indan-1-one (400 mg, 1.90 mmol) in DMF (5 ml) was added sodium azide (1.98 g, 0.03 mol). The reaction was allowed to stir at room temperature for 15 mins. The product was partitioned between water (10 ml) and ether (10 ml). The ether layers were combined and the crude reaction mixture was passed through a plug of flash silica, eluting with petroleum ether:ethyl acetate (9:1). The product was isolated as an orange oil (283 mg, 86%).

Workup

  1. customThe product was partitioned between water (10 ml) and ether (10 ml)
  2. customthe crude reaction mixture
  3. washeluting with petroleum ether:ethyl acetate (9:1)

Sources & evidence

ORD record
ord-eed564b2fbf242f284c2735251596e23
Source dataset
uspto-grants-2001_10
Patent number
US06297399B1

Linked notes

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