Phosphorus oxychloride → 5-Chlorotetrazolo(1,5-a][1,7]naphthyridine

HRID 47461Notes

Reaction equation

HRID 47461 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]=[N:8][CH:7]=3.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:12]1[C:11]2[C:6](=[CH:7][N: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 178515416HCID 178515416, compound

Product 1

HCID 120158005-Chlorotetrazolo(1,5-a][1,7]naphthyridine

Conditions

Temperature
90 °C

Procedure

A suspension of tetrazolo[1,5-a][1,7]naphthyridin-5-ol (3.5 g) in phosphorous oxychloride (15 mL) was heated at 90° C. for 2 hours. The reaction mixture was concentrated under vacuum. The residue was poured into ice water, dichloromethane was added followed by the addition of 10% sodium hydroxide to neutral pH. The product was partitioned into dichloromethane. The dichloromethane layer was separated, dried over magnesium sulfate then concentrated under vacuum to provide 3.8 g of 5-chlorotetrazolo[1,5-a][1,7]naphthyridine as a solid, m.p. 176-177° C. Analysis: Calculated for C8H4ClN5: %C, 46.73; %H, 1.96; %N, 34.06. Found: %C, 46.80; %H, 2.16; %N, 34.45.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additionThe residue was poured into ice water, dichloromethane
  3. additionwas added
  4. additionfollowed by the addition of 10% sodium hydroxide to neutral pH
  5. customThe product was partitioned into dichloromethane
  6. customThe dichloromethane layer was separated
  7. dry with materialdried over magnesium sulfate
  8. concentrationthen concentrated under vacuum

Sources & evidence

ORD record
ord-94b20cc68299473f860d9e6dd2d9bbe0
Source dataset
uspto-grants-2004_03
Patent number
US06699878B2

Reaction notes

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