Ammonium → HCID 481003, compound

HRID 1840724Notes

Reaction equation

HRID 1840724 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([CH3:28])[CH:27]=1)[CH2:6][C:7]1[C:12]([CH2:13][CH3:14])=[C:11]([CH3:15])[N:10]=[C:9]([O:16]C)[C:8]=1[NH:18]C(=O)C(C)(C)C.[NH4+]>O>[NH2:18][C:8]1[C:9](=[O:16])[NH:10][C:11]([CH3:15])=[C:12]([CH2:13][CH3:14])[C:7]=1[CH2:6][C:5]1[CH:4]=[C:3]([CH3:2])[CH:27]=[C:26]([CH3:28])[CH:25]=1

Participants

5

Reactant 3

HCID 223AmmoniumHCID 313Hydrochloric AcidHCID 481000HCID 481000, compound

Product 1

HCID 481003HCID 481003, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3M aqueous hydrochloric acid (150 mL) was added to a suspension of 4-(3,5-dimethylbenzyl)-5-ethyl-2-methoxy-6-methyl-3-pivaloylaminopyridine (2.36 g) in water (300 mL). The mixture was refluxed for 3.5 h and then stirred at room temperature for 12 h. The solution was basified by adding concentrated ammonium hydroxyde and was extracted with 3×800 mL ethyl acetate. The combined organic layers were washed with 110 mL brine, dried over magnesium sulfate and concentrated under reduced pressure giving 3-amino-4-(3,5-dimethylbenzyl)-5-ethyl-6-methylpyridin-2(1H)-one. (1.79 g, 100%). mp 204-205° C.

Workup

  1. temperatureThe mixture was refluxed for 3.5 h
  2. extractionwas extracted with 3×800 mL ethyl acetate
  3. washThe combined organic layers were washed with 110 mL brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8685a1e5da5e4ad68bdef41ab0f493e2
Source dataset
uspto-grants-2004_01
Patent number
US06683079B2

Reaction notes

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