Hydrochloric Acid → 4(1H)-Pyridinone, 2-(aminomethyl)-1,6-dimethyl-3-(phenylmethoxy)-

HRID 2280240Notes

Reaction equation

HRID 2280240 reaction equation
[CH3:1][N:2]1[C:7]([CH3:8])=[CH:6][C:5](=[O:9])[C:4]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:3]1[CH2:18][N:19]1C(=O)C2=CC=CC=C2C1=O.O.Cl>CCO>[CH3:1][N:2]1[C:7]([CH3:8])=[CH:6][C:5](=[O:9])[C:4]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:3]1[CH2:18][NH2:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 11069145HCID 11069145, compound

Product 1

HCID 111397854(1H)-Pyridinone, 2-(aminomethyl)-1,6-dimethyl-3-(phenylmethoxy)-Yield 92.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
4 °C

Procedure

10 g of 59 (26 mmol, 1 equiv) was dissolved in 100 ml EtOH. 17 ml N2H4 (5.5% aqueous) was added and the solution was refluxed for 3 hours. 59 did not fully dissolve until refluxing had begun. The solution was allowed to cool, at which point it solidified. Water was added and the pH adjusted to 1 with conc. HCl. After overnight cooling at 4° C., the solution was filtered. The pH of the filtrate was adjusted to 14 with 10 N NaOH and extracted with 5×100 ml CH2Cl2. The extracts were combined and dried over Na2SO4. The solvent was removed in vacuo to give 6.2 g of a white solid in 92% yield.

Workup

  1. temperaturethe solution was refluxed for 3 hours
  2. dissolution59 did not fully dissolve
  3. temperatureuntil refluxing
  4. temperatureto cool, at which point it
  5. filtrationthe solution was filtered
  6. extractionextracted with 5×100 ml CH2Cl2
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4ec19b02f7674d869d5e44434de3ce76
Source dataset
uspto-grants-2015_09
Patent number
US09138495B2

Reaction notes

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