Water → 2-Azido-1-oxo-1lambda~5~-quinoline

HRID 435740Notes

Reaction equation

HRID 435740 reaction equation
Cl.Cl[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N+:4]=1[O-:13].[N-:14]=[N+:15]=[N-:16].[Na+].O>CC(C)=O>[N:14]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N+:4]=1[O-:13])=[N+:15]=[N-:16]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 21481204136545-12-5

Product 1

HCID 126998242-Azido-1-oxo-1lambda~5~-quinoline

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In this example, 2.00 grams (0.009 mol) of 2-chloroquinoline N-oxide hydrochloride and 2.00 grams (0.031 mol) of sodium azide were added to and dissolved in 50 ml. of water and 100 ml. of acetone and the resulting solution stirred for 72 hours at 25° C. A solid separated and was collected by filtration. Recrystallization of this solid from benzene gave 2-azidoquinoline N-oxide in a yield of 1.01 grams or 58% of theory having a melting point of 103.5° C. to 104.5° C. with decomposition.

Workup

  1. dissolutiondissolved in 50 ml
  2. customA solid separated
  3. filtrationwas collected by filtration
  4. customRecrystallization of this solid from benzene

Sources & evidence

ORD record
ord-d2329f2964394517995e3d7e4c5df4d0
Source dataset
uspto-grants-1977_02
Patent number
US04006160

Reaction notes

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