6-Methylquinoline → HCID 19000317, compound

HRID 2260337Notes

Reaction equation

HRID 2260337 reaction equation
[CH3:1][C:2]([N:5]1[N:9]=[N:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:6]1)([CH3:4])[CH3:3].O1CCCC1.C([Li])CCC.[CH3:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[N:33]=[CH:32][CH:31]=[CH:30]2>CCCCCC.C1(C)C=CC=CC=1.C(O)C>[CH3:4][C:2]([N:5]1[N:9]=[N:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH:32]2[CH:31]=[CH:30][C:29]3[C:34](=[CH:35][CH:36]=[C:27]([CH3:26])[CH:28]=3)[NH:33]2)=[N:6]1)([CH3:1])[CH3:3]

Participants

8

Reactant 4

HCID 70596-MethylquinolineHCID 8028TetrahydrofuranHCID 671797ST047279HCID 178418339Butyllithium

Product 1

HCID 19000317HCID 19000317, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

100 g (490 mmol) of 2-(1,1-dimethylethyl)-5-phenyl-2H-tetrazole and 500 ml of anhydrous tetrahydrofuran are introduced into a 2-liter three-necked round-bottomed flask under a nitrogen atmosphere. 215 ml (580 mmol) of 2.5M n-butyllithium solution in hexane are added dropwise to the mixture. The mixture is heated at the reflux temperature for 45 minutes, followed by addition of 49 g (410 mmol) of 6-methylquinoline dissolved in 300 ml of toluene. The reaction medium is left for 2 hours at the reflux temperature and is then cooled to room temperature. Next, 300 ml of ethanol are added and the solvent is evaporated off under reduced pressure. The residue is taken up in 500 ml of water and is filtered, washed with 200 ml of isopropanol and dried under vacuum.

Workup

  1. temperatureThe mixture is heated at the reflux temperature for 45 minutes
  2. customthe solvent is evaporated off under reduced pressure
  3. filtrationis filtered
  4. washwashed with 200 ml of isopropanol
  5. customdried under vacuum

Sources & evidence

ORD record
ord-be96560ab0134b5fbea44eb2c0751c28
Source dataset
uspto-grants-1995_12
Patent number
US05476941

Reaction notes

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