Ammonia → HCID 21555760, compound

HRID 267230Notes

Reaction equation

HRID 267230 reaction equation
[ClH:1].[CH2:2]([C:9]1[N:14]=[C:13]([C:15]([C:17]2[CH:22]=[C:21]([O:23]C)[CH:20]=[C:19]([O:25]C)[CH:18]=2)=[O:16])[CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br.N>>[ClH:1].[CH2:2]([C:9]1[N:14]=[C:13]([C:15]([C:17]2[CH:22]=[C:21]([OH:23])[CH:20]=[C:19]([OH:25])[CH:18]=2)=[O:16])[CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 260Hydrogen BromideHCID 21555753HCID 21555753, compound

Product 1

HCID 21555760HCID 21555760, compound

Procedure

About 15.5 g. of 3,5-dimethoxyphenyl 6-benzyl-2-pyridyl ketone hydrochloride in 55 ml. of constant boiling hydrobromic acid were heated under reflux for 12 hours. Removal of the solvent gave a tacky residue which was basified with ammonia solution and was extracted three times with a total of 90 ml. of boiling ethyl acetate. The extracts were washed twice with a total of 50 ml. of water, dried over magnesium sulfate and treated with charcoal. Removal of the solids and treatment of the filtrate with hydrogen chloride yielded 3.52 g. of a khaki-colored salt. Nuclear magnetic spectroscopy revealed that the methoxy groups had been removed and the product was used without further purification for the next step.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 12 hours
  3. customRemoval of the solvent
  4. customgave a tacky residue which
  5. extractionwas extracted three times with a total of 90 ml
  6. washThe extracts were washed twice with a total of 50 ml
  7. dry with materialof water, dried over magnesium sulfate
  8. additiontreated with charcoal
  9. customRemoval of the solids and treatment of the filtrate with hydrogen chloride
  10. customyielded 3.52 g
  11. customhad been removed
  12. customthe product was used without further purification for the next step

Sources & evidence

ORD record
ord-d5f0f705b37e48b1b715f418cbdede6f
Source dataset
uspto-grants-1976_03
Patent number
US03941796

Reaction notes

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