Sodium Carbonate → 4-Methyl-5-pentyl-2-pyridinamine

HRID 1740941Notes

Reaction equation

HRID 1740941 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:6][N:5]=[C:4]([NH:13]C(=O)C(C)(C)C)[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl>[CH2:8]([C:7]1[C:2]([CH3:1])=[CH:3][C:4]([NH2:13])=[N:5][CH:6]=1)[CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 21834422HCID 21834422, compound

Product 1

HCID 98989924-Methyl-5-pentyl-2-pyridinamine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 4-methyl-2-(trimethylacetyl)amino-5-(1-pentyl)-pyridine (233 mg, 0.89 mmol) in 2N hydrochloric acid (3 mL) was heated at 100° C. for 18 h. The solution was cooled to room temperature, made basic with 20% aqueous sodium carbonate and extracted with chloroform. The organic layer was dried (Na2SO4), and evaporated. The product was purified by silica gel column chromatography using 2% methanol/methylene chloride to give the title compound.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customevaporated
  5. customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5a3337f9291043979b1013cb8aae1d59
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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