Potassium Carbonate → HCID 12235832, compound

HRID 2163500Notes

Reaction equation

HRID 2163500 reaction equation
[Cl-].[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N+:4]=1[CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1Br.C(=O)([O-])[O-].[K+].[K+]>C(O)CC.O>[CH:15]1[C:16]2[N:2]=[C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][N:4]3[CH2:9][O:10][C:11]=2[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 22752766HCID 22752766, compound

Product 1

HCID 12235832HCID 12235832, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10311-PropanolSolvent

Procedure

A mixture of 9.5 g of 2-amino-1-[(o-bromophenoxy)methyl]pyridinium chloride, 8.3 g of potassium carbonate, 0.4 g of copper-bronze in 150 ml of n-propanol and 25 ml of water under N2, is heated under reflux for 12 hours while stirring. The mixture is filtered hot and the deep yellow filtrate is concentrated to dryness. The residue is dissolved in 400 ml of ether, the ether solution is washed, dried and the solvent removed to give about 6.4 g of the crude yellow product. This is recrystallized from cyclohexane to give about 3.6 g of the title product, mp about 125°-127°.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 12 hours
  3. filtrationThe mixture is filtered hot
  4. concentrationthe deep yellow filtrate is concentrated to dryness
  5. dissolutionThe residue is dissolved in 400 ml of ether
  6. washthe ether solution is washed
  7. customdried
  8. customthe solvent removed
  9. customto give about 6.4 g of the crude yellow product
  10. customThis is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-af0fb47cc9344db290e9a568b627eac7
Source dataset
uspto-grants-1979_01
Patent number
US04134975

Reaction notes

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