Water → HCID 18439912, compound

HRID 1394120Notes

Reaction equation

HRID 1394120 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[CH:6]=[C:5]2Cl.CN1C(=O)CCC1.[N-:27]=[N+:28]=[N-:29].[Na+].O>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[CH:6]=[C:5]2[N:27]=[N+:28]=[N-:29]

Participants

6

Reactant 4

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 33557Sodium AzideHCID 11209906HCID 11209906, compound

Product 1

HCID 18439912HCID 18439912, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

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

Workup

  1. customInto a 250 mL three-neck round-bottom flask equipped with a condenser, magnetic stirrer, silicone oil heating bath, nitrogen inlet and gas outlet
  2. temperatureAt the end of this time the reaction was cooled
  3. additionpoured into a 1 L separatory funnel
  4. customwere separated
  5. extractionThe aqueous layer was then extracted twice with 100 mL of ethyl acetate
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a product, which
  10. customwas carried to the next step without further purification

Sources & evidence

ORD record
ord-1d4a9f60ee0e4e13861c986288118cca
Source dataset
uspto-grants-2008_03
Patent number
US07348340B2

Reaction notes

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