Sodium Azide → HCID 57722697, compound

HRID 1987063Notes

Reaction equation

HRID 1987063 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[CH:10]2)=[O:4].[N-:15]=[N+:16]=[N-:17].[Na+]>CS(C)=O.CCOC(C)=O>[N:15]([CH2:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[CH:10]2)=[O:4])=[N+:16]=[N-:17]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 14722778HCID 14722778, compound

Product 1

HCID 57722697HCID 57722697, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-1-quinolin-8-yl-ethanone (5.85 g, 28.5 mmol) in DMSO (60 mL), as prepared in the last step, was added NaN3 (2.2 g, 33.9 mmol). After 2 hours, the reaction was diluted with EtOAc (250 mL) and washed with H2O (3×100 mL). The organic phase was washed with brine (100 mL), dried over Na2SO4 and concentrated in vacuo. Purification via SiO2 chromatography (20% EtOAc/hexanes) affored the product as a pale yellow solid (4.95 g). 1H NMR (300 Hz, CDCl3) δ 9.0-8.97 (m, 1H), 8.26-8.22 (m, 2H), 8.04-8.02 (m, 1H), 7.68-7.63 (m, 1H), 7.52-7.48 (m, 1H), 5.12 (s, 2H).

Workup

  1. washwashed with H2O (3×100 mL)
  2. washThe organic phase was washed with brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification via SiO2 chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f84a0735d3894370a066fd26ec074093
Source dataset
uspto-grants-2009_06
Patent number
US07550474B2

Reaction notes

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