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

HRID 1086239Notes

Reaction equation

HRID 1086239 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-5195125e6ce24043a7c5a6f94f42acd8
Source dataset
uspto-grants-1991_07
Patent number
US05028615

Reaction notes

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