Pyridine → HCID 178422718, compound

HRID 25896Notes

Reaction equation

HRID 25896 reaction equation
[CH3:1][C:2]1[C:11]([C:12]([OH:14])=O)=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.O.[NH2:16][C:17]1[NH:21][N:20]=[N:19][N:18]=1.N1C=CC=CC=1.S(Cl)(Cl)=O>O.C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:11]([C:12](=[O:14])[NH:16][C:17]2[NH:21][N:20]=[N:19][N:18]=2)=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 10702733HCID 10702733, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178422718HCID 178422718, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 4.7 g. (0.026 mole) of 7-methyl-8-quinolinecarboxylic acid, 3.9 g. (0.037 mole) of 5-aminotetrazole hydrate in 30 ml. of pyridine and 50 ml. of chloroform is added dropwise with stirring 5.6 ml. of thionyl chloride. The mixture is stirred at 70° C. for about one hour. The reaction mixture is evaporated to provide a residue which is diluted with water. The precipitate is separated by filtration and recrystallized from acetic acid. The product is again recrystallized from ethanol to provide 7-methyl-8-(1H-tetrazole-5-ylcarbamoyl)quinoline, m.p. 285°-287° C.

Workup

  1. stirringThe mixture is stirred at 70° C. for about one hour
  2. customThe reaction mixture is evaporated
  3. customto provide a residue which
  4. customThe precipitate is separated by filtration
  5. customrecrystallized from acetic acid
  6. customThe product is again recrystallized from ethanol

Sources & evidence

ORD record
ord-c5611fa7aee94ce4a78a16dbd431a99b
Source dataset
uspto-grants-1979_04
Patent number
US04147694

Reaction notes

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