Phosphorus oxychloride → 5-Chlorotetrazolo[1,5-a][1,8]naphthyridine

HRID 2181939Notes

Reaction equation

HRID 2181939 reaction equation
[N:1]1[N:5]2[C:6]3[C:11]([C:12](O)=[CH:13][C:4]2=[N:3][N:2]=1)=[CH:10][CH:9]=[CH:8][N:7]=3.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:12]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]2[N:1]=[N:2][N:3]=[C:4]2[CH:13]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178515417HCID 178515417, compound

Product 1

HCID 221727235-Chlorotetrazolo[1,5-a][1,8]naphthyridine

Procedure

Tetrazolo[1,5-a][1,8]naphthyridin-5-ol (0.5 g, 2.67 mmole) was suspended in phosphorous oxychloride (10 mL) and heated at reflux for 4 hours. The reaction mixture was concentrated under vacuum and the residue was poured into water. Dichloromethane was added and the aqueous layer was made basic with sodium bicarbonate. The dichloromethane layer was separated, dried over magnesium sulfate, filtered and then concentrated under vacuum. The resulting solid was recrystallized from toluene to provide 0.3 g of 5-chlorotetrazolo[1,5-a][1,8]naphthyridine as a solid, m.p. 229-230° C. (decomposition). Analysis: Calculated for C8H4ClN5: % C, 46.73; % H, 1.96; % N, 34.06; Found: % C, 46.87; % H, 1.54; % N, 33.93.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. additionthe residue was poured into water
  5. additionDichloromethane was added
  6. customThe dichloromethane layer was separated
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe resulting solid was recrystallized from toluene

Sources & evidence

ORD record
ord-1c8c2c9daa3b41beb02cbacc7b33de66
Source dataset
uspto-grants-2005_05
Patent number
US06894165B2

Reaction notes

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