Potassium Hydroxide → HCID 178420714, compound

HRID 2351868Notes

Reaction equation

HRID 2351868 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[O:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1.Cl[CH2:21][CH2:22][CH2:23][C:24]1[NH:28][N:27]=[N:26][N:25]=1.[OH-].[K+]>O.C(O)C.CCCCCC.C(OCC)(=O)C>[N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[CH2:6][O:5][C:4]1[CH:3]=[C:2]([CH:19]=[CH:18][CH:17]=1)[O:1][CH2:21][CH2:22][CH2:23][C:24]1[NH:28][N:27]=[N:26][N:25]=1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 10988736Phenol, 3-(2-quinolinylmethoxy)-HCID 178478461HCID 178478461, compound

Product 1

HCID 178420714HCID 178420714, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 3.51 g (0.014 mol) 2-[(3-hydroxyphenoxy)methyl]quinoline, 2.04 g (0.14 mol) 5-(3-chloropropyl)tetrazole and 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. 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 (55:45) as eluent. Evaporation of eluent gives 5-[3-(3-(2-quinolylmethyloxy)phenoxy)propyl]tetrazole (M.P. 147°-149° C.).

Workup

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

Sources & evidence

ORD record
ord-e262a63d326c4acb8d1f4c539afa6e2e
Source dataset
uspto-grants-1989_10
Patent number
US04874769

Reaction notes

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