Phosphorus oxychloride → 5-Chloro-4-nitrotetrazolo[1,5-a]quinoline

HRID 432699Notes

Reaction equation

HRID 432699 reaction equation
O=P(Cl)(Cl)[Cl:3].[N+:6]([C:9]1[C:10]2[N:11]([N:20]=[N:21][N:22]=2)[C:12]2[C:17]([C:18]=1O)=[CH:16][CH:15]=[CH:14][CH:13]=2)([O-:8])=[O:7]>CN(C)C=O>[Cl:3][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]2[N:20]=[N:21][N:22]=[C:10]2[C:9]=1[N+:6]([O-:8])=[O:7]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526872HCID 178526872, compound

Product 1

HCID 27868695-Chloro-4-nitrotetrazolo[1,5-a]quinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, POCl3 (16.42 ml, 0.17 mol) was slowly added to a chilled (0° C.) flask containing N,N-dimethylformamide (100 ml). The resulting solution was slowly warmed to room temperature and then added dropwise to a suspension of 4-nitro-tetrazolo[1,5-a]quinolin-5-ol in N,N-dimethylformamide (300 ml). The reaction was heated to 100° C. for 30 minutes. The orange/red solution was quenched by pouring over 1 liter of ice water. A yellow precipitate formed and was collected by filtration, redissolved in chloroform (approx. 750 ml), dried (Na2SO4), filtered, and concentrated in vacuo to yield 33.74 g of 5-chloro-4-nitrotetrazolo[1,5-a]quinoline as a yellow solid.

Workup

  1. temperatureThe resulting solution was slowly warmed to room temperature
  2. temperatureThe reaction was heated to 100° C. for 30 minutes
  3. customThe orange/red solution was quenched
  4. additionby pouring over 1 liter of ice water
  5. customA yellow precipitate formed
  6. filtrationwas collected by filtration
  7. dissolutionredissolved in chloroform (approx. 750 ml)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa007614e45b48dcba09a2d9a93b3ea6
Source dataset
uspto-grants-2003_12
Patent number
US06664260B2

Reaction notes

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