Sodium Azide → 3-azidomethyl-7-chloro-1-phenyl-1H-quinolin-4-one

HRID 1887797Notes

Reaction equation

HRID 1887797 reaction equation
Br[CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([Cl:14])=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:4]=1.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C=O)C>[N:21]([CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][C:8]([Cl:14])=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:4]=1)=[N+:22]=[N-:23]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 866757643-bromomethyl-7-chloro-1-phenyl-1H-quinolin-4-one

Product 1

HCID 712080783-azidomethyl-7-chloro-1-phenyl-1H-quinolin-4-oneYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 25 mL round-bottomed flask, crude 3-bromomethyl-7-chloro-1-phenyl-1H-quinolin-4-one (0.184 g, 0.528 mmol) and sodium azide (34.3 mg, 0.528 mmol) were combined with DMF (3.5 mL) to give a yellow solution. The reaction mixture was stirred overnight at room temperature. The reaction mixture was poured over ice and the resulting white suspension was extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered, then concentrated to afford the crude product as slightly yellow oil. The crude was purified by flash chromatography using 15%-45% ethyl acetate/hexanes to afford 3-azidomethyl-7-chloro-1-phenyl-1H-quinolin-4-one (75 mg, 46% yield) as a white solid.

Workup

  1. customto give a yellow solution
  2. additionThe reaction mixture was poured over ice
  3. extractionthe resulting white suspension was extracted with ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford the crude product as slightly yellow oil
  8. customThe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-969dcf01ece04811a0d711a6c1972e0d
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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