Dimethylformamide → HCID 178515419, compound

HRID 258812Notes

Reaction equation

HRID 258812 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]#[N:13])=[C:7]2[OH:14].[N-:15]=[N+:16]=[N-:17].[Na+].[Cl-].[NH4+].CN(C)C=O>Cl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12]1[NH:17][N:16]=[N:15][N:13]=1)=[C:7]2[OH:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 178510282HCID 178510282, compound

Product 1

HCID 178515419HCID 178515419, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

a mixture of 22 g. (90 mmoles) of 8-bromo-3-cyano-4-hydroxyquinoline (from Example 1), 7.0 g. (108 mmoles) of sodium azide and 6.0 g. (112 mmoles) of ammonium chloride in 300 ml. of N,N-dimethylformamide is heated at a bath termperature of 125° C. for about 16 hours. The mixture is then diluted with 5 percent aqueous hydrochloric acid, filtered and the insoluble product is dried to provide 8-bromo-4-hydroxy-3-(1H-tetrazole-5-yl)quinoline, m.p. >260° C. Analysis: Calculated for C10H6BrN5O: %C, 41.12; %H, 2.07; %N, 23.98. Found: %C, 41.0; %H, 2.0; %N, 23.8.

Workup

  1. additiona mixture of 22 g
  2. filtrationfiltered
  3. customthe insoluble product is dried

Sources & evidence

ORD record
ord-0211d46b1a2c4573a876cbd558a89c7e
Source dataset
uspto-grants-1977_07
Patent number
US04035368

Reaction notes

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