Pyridine → 8-(1-methyl-1H-tetrazole-5-ylcarbamoyl)quinoline

HRID 2052672Notes

Reaction equation

HRID 2052672 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([OH:13])=O)[CH:4]=[CH:3][CH:2]=1.[NH2:14][C:15]1[N:19]([CH3:20])[N:18]=[N:17][N:16]=1.N1C=CC=CC=1.S(Cl)(Cl)=O>O>[CH3:20][N:19]1[C:15]([NH:14][C:11]([C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[N:1]=[CH:2][CH:3]=[CH:4]3)=[O:13])=[N:16][N:17]=[N:18]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 665828-Quinolinecarboxylic acidHCID 1384921-methyl-1H-tetrazol-5-amine

Product 1

HCID 131923048-(1-methyl-1H-tetrazole-5-ylcarbamoyl)quinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2.4 g. (0.020 mole) of 8-quinoline- carboxylic acid and 3.0 g. (0.030 mole) of 5-amino-1-methyltetrazole is stirred in 30 ml. of pyridine at 20° C. while adding 2.0 ml. of thionyl chloride dropwise. The mixture is heated at 70° C. for one hour. The reaction mixture is evaporated to provide a residue which is diluted with water. The solid is separated by filtration and recrystallized from acetic acid with decolorizing charcoal. The product is recrystallized a second time from acetic acid to provide 8-(1-methyl-1H-tetrazole-5-ylcarbamoyl)quinoline, m.p. 224°-225° C.

Workup

  1. additionA mixture of 2.4 g
  2. customThe reaction mixture is evaporated
  3. customto provide a residue which
  4. customThe solid is separated by filtration
  5. customrecrystallized from acetic acid with decolorizing charcoal
  6. customThe product is recrystallized a second time from acetic acid

Sources & evidence

ORD record
ord-7452a940fb5e4161b50444c439678a20
Source dataset
uspto-grants-1980_01
Patent number
US04186201

Reaction notes

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