Water → HCID 22643263, compound

HRID 2414758Notes

Reaction equation

HRID 2414758 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[CH:8]=[C:7]2Cl)([O-:3])=[O:2].CN1C(=O)CCC1.[N-:29]=[N+:30]=[N-:31].[Na+].O>C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[CH:8]=[C:7]2[N:29]=[N+:30]=[N-:31])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 33557Sodium AzideHCID 22643158HCID 22643158, compound

Product 1

HCID 22643263HCID 22643263, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

6-Nitro-4-chloro-2-(3-fluorophenyl)-quinoline 3.2 g (9.50 mmoles) was placed in a 250 mL three neck round bottom flask equipped with a condenser, magnetic stirrer, silicone oil heating bath, nitrogen inlet and gas outlet. To this was added 75 mL of N-methyl pyrrolidinone then 6.0 g (95 mmoles, 10 equiv.) of sodium azide. The mixture was stirred and warmed to 60° C. for 18 hr. After this time the mixture was cooled, poured into a 1 L separatory funnel containing 500 mL water and 250 mL of ethyl acetate. The pH was adjusted to 9.0 and the layers separated. The aqueous layer was extracted twice with 100 mL of ethyl acetate, the organic layers combined, dried over Na2SO4, filtered and concentrated to yield a product, which was carried to the next step without further purification.

Workup

  1. customequipped with a condenser, magnetic stirrer, silicone oil heating bath, nitrogen inlet and gas outlet
  2. temperatureAfter this time the mixture was cooled
  3. additionpoured into a 1 L separatory funnel
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted twice with 100 mL of ethyl acetate
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield a product, which
  10. customwas carried to the next step without further purification

Sources & evidence

ORD record
ord-9378255021c9464db75172fab67a1b9e
Source dataset
uspto-grants-2004_11
Patent number
US06815447B2

Reaction notes

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