Dimethylformamide → 3-azidomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-one

HRID 1887806Notes

Reaction equation

HRID 1887806 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][C:16]=2[Cl:21])[CH:4]=1.[N-:22]=[N+:23]=[N-:24].[Na+].CN(C=O)C>C(OCC)(=O)C>[N:22]([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][C:16]=2[Cl:21])[CH:4]=1)=[N+:23]=[N-:24]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 866757663-bromomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-one

Product 1

HCID 712086763-azidomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-oneYield 58.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 25 mL round-bottom flask containing the crude 3-bromomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-one (410 mg, 1.07 mmol) was added sodium azide (83.5 mg, 1.28 mmol) and DMF (9 mL). The reaction mixture was stirred overnight at room temperature. The mixture was diluted with ethyl acetate (100 mL) and washed with brine (100 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated. The crude was purified by flash chromatography (silica gel, 24 g, 0-50% ethyl acetate in hexanes) to yield 3-azidomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-one (215 mg, 58%) as a light yellow solid. 1H NMR (DMSO-d6) δ ppm 8.17-8.36 (m, 2H) 7.83 (ddd, J=9.8, 7.9, 1.7 Hz, 2H) 7.68 (ddd, J=9.8, 7.8, 1.6 Hz, 2H) 7.48 (dd, J=8.7, 1.8 Hz, 1H) 6.70 (d, J=1.8 Hz, 1H) 4.09-4.44 (m, 2H). MS calcd. for C16H10Cl2N4O [(M+H)+] 346.0, obsd. 345.0.

Workup

  1. washwashed with brine (100 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude was purified by flash chromatography (silica gel, 24 g, 0-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-46b9c8e864ed4dd5804ade0684c85239
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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