Sodium Azide → 4-Azido-5,8-difluoro-2-methylquinoline

HRID 47425Notes

Reaction equation

HRID 47425 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([F:13])[CH:8]=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([CH3:14])[CH:3]=1.[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C)C=O>[N:15]([C:2]1[C:11]2[C:6](=[C:7]([F:13])[CH:8]=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([CH3:14])[CH:3]=1)=[N+:16]=[N-:17]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 227451704-Chloro-5,8-difluoro-2-methyl-quinoline

Product 1

HCID 227451444-Azido-5,8-difluoro-2-methylquinolineYield 64.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-5,8-difluoro-2-methylquinoline (8.18 g) in dimethylformamide (80 ml) was treated with sodium azide (3.7 g) and the mixture heated for 20 h. The mixture was cooled, poured into ice/water and extracted with dichloromethane (2×200 ml). The organic phase was washed with water, dried (Na2SO4) and solvent removed at reduced pressure. The residue was column chromatographed (silica gel (5-20% diethyl ether in pentane) to give the title compound (5.45 g) as a colourless solid. (Method C). 1H NMR δ: 2.67 (3H, s), 7.29 (1H, m), 7.54 (1H, s), 7.58(1H, m).

Workup

  1. temperaturethe mixture heated for 20 h
  2. temperatureThe mixture was cooled
  3. extractionextracted with dichloromethane (2×200 ml)
  4. washThe organic phase was washed with water
  5. dry with materialdried (Na2SO4) and solvent
  6. customremoved at reduced pressure
  7. customchromatographed (silica gel (5-20% diethyl ether in pentane)

Sources & evidence

ORD record
ord-5559132f7074456ba1d69992d585c31a
Source dataset
uspto-grants-2004_03
Patent number
US06699879B1

Reaction notes

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