Ethanol → 5-(3-(4-(4-(2-Quinolinylmethyloxy)styryl)phenoxy)propyl)tetrazole

HRID 373952Notes

Reaction equation

HRID 373952 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:27]=[CH:26][C:16]([CH:17]=[CH:18][C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.Cl[CH2:29][CH2:30][CH2:31][C:32]1[NH:36][N:35]=[N:34][N:33]=1.[OH-].[K+].C(O)C>O.CCCCCC.C(OCC)(=O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:27]=[CH:26][C:16]([CH:17]=[CH:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:29][CH2:30][CH2:31][C:32]3[NH:36][N:35]=[N:34][N:33]=3)=[CH:23][CH:24]=2)=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 539691924-(4-(2-Quinolinylmethyloxy)styryl)phenolHCID 178478461HCID 178478461, compound

Product 1

HCID 1784366615-(3-(4-(4-(2-Quinolinylmethyloxy)styryl)phenoxy)propyl)tetrazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of (0.014 mol) 4-(4-(2-quinolinylmethyloxy)styryl)phenol, (0.14 mol) 5-(3-chloropropyl)tetrazole, 2 g (0.036 mol) KOH in 5 ml water, and 50 ml ethanol is heated over a steam bath for a period of 3 hours. The reaction mixture is concentrated to dryness and slurried into water and extracted with methylene chloride. The methylene chloride extract is washed with water, dried over MgSO4 and concentrated under reduced pressure to obtain solid which is passed through a silica gel column using hexane/ethyl acetate as eluent. Evaporation of eluent gives 5-(3-(4-(4-(2-quinolinylmethyloxy)styryl)phenoxy)propyl)tetrazole.

Workup

  1. temperatureis heated over a steam bath for a period of 3 hours
  2. concentrationThe reaction mixture is concentrated to dryness
  3. extractionextracted with methylene chloride
  4. extractionThe methylene chloride extract
  5. washis washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customto obtain solid which
  9. customEvaporation of eluent

Sources & evidence

ORD record
ord-0a8c38fe4f054f18a6a8aeffc64a5ca7
Source dataset
uspto-grants-1992_11
Patent number
US05166210

Reaction notes

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