1-Bromopropane → HCID 12807894, compound

HRID 543697Notes

Reaction equation

HRID 543697 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[CH2:12][OH:13].C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[CH2:21][CH3:22]>CC(=O)CC>[OH:13][CH2:12][C:3]1[C:2](=[O:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:20][CH2:21][CH3:22])[CH:4]=1

Participants

5

Reactant 3

HCID 78401-Bromopropane2×HCID 11430Potassium CarbonateHCID 178519804HCID 178519804, compound

Product 1

HCID 12807894HCID 12807894, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-hydroxy-3-hydroxymethylquinoline (5.0 g.), anhydrous potassium carbonate (1.6 g.), propyl bromide (2.6 ml.) and 2-butanone (500 ml.) was stirred and boiled under reflux for 18 hours. Additional propyl bromide (2 ml.) was added and the mixture boiled under reflux for 23 hours. The solvent was evaporated and the residue treated with water (100 ml.) and basified with 5 N aqueous sodium hydroxide. The solution was extracted with dichloromethane (4×100 ml.). The extract was dried and evaporated to give an oil. This oil was triturated with petroleum ether:ethyl acetate:industrial methylated spirit 12:1:1 to give the novel compound 3-hydroxymethyl-1-propyl-4-quinolone, m.p. 88°-91°.

Workup

  1. temperatureunder reflux for 18 hours
  2. temperatureunder reflux for 23 hours
  3. customThe solvent was evaporated
  4. additionthe residue treated with water (100 ml.)
  5. extractionThe solution was extracted with dichloromethane (4×100 ml.)
  6. customThe extract was dried
  7. customevaporated
  8. customto give an oil
  9. customThis oil was triturated with petroleum ether:ethyl acetate:industrial methylated spirit 12:1:1

Sources & evidence

ORD record
ord-f1b29dfc46994ade89c320dc54d0ba5f
Source dataset
uspto-grants-1984_05
Patent number
US04447435

Reaction notes

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