Sodium Azide → 7-Bromo-1,2,3,9b-tetraaza-cyclopenta[a]naphthalene

HRID 2075714Notes

Reaction equation

HRID 2075714 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](Cl)[CH:6]=[CH:5]2.[N-:13]=[N+:14]=[N-:15].[Na+]>CN(C=O)C.CCOC(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[N:13]=[N:14][N:15]=[C:7]1[CH:6]=[CH:5]2

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 128940866-Bromo-2-chloroquinoline

Product 1

HCID 582578107-Bromo-1,2,3,9b-tetraaza-cyclopenta[a]naphthalene

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

To 6-Bromo-2-chloro-quinoline (223 mg, 1.0 mmol) in DMF (10 mL) was added sodium azide (65 mg, 1.0 mmol). The reaction was heated at 130° C. for 1 hour, then cooled to room temperature and diluted with EtOAc and water. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The crude material was purified by silica gel chromatography (50% EtOAc in hexanes) to give the desired product, 9d.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by silica gel chromatography (50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-691c40f929d640088fd1f6c62ea870fd
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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