2-Amino-4-methylpyridine → 4-Methyl-2-phthalimidopyridine

HRID 726667Notes

Reaction equation

HRID 726667 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[C:9]1(=O)[O:14][C:12](=[O:13])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12.C(OC(=O)C)(=O)C>C(O)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[C:12](=[O:13])[C:11]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]3[C:9]2=[O:14])[CH:3]=1

Participants

5

Reactant 3

HCID 15332-Amino-4-methylpyridineHCID 6811Phthalic AnhydrideHCID 7918Acetic Anhydride

Product 1

HCID 109990494-Methyl-2-phthalimidopyridineYield 42.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirring solution of 4-methyl-2-aminopyridine (50 g, 460 mmol) in acetic acid (1 L) was added phthalic anhydride (68 g, 460 mmol) and the reaction was heated to reflux. After 12 h, acetic anhydride (43 mL, 460 mmol) was added and the solution continued to stir at reflux for an additional 48 h. The solvent was then removed in vacuo and the solid residue was suspended in toluene and concentrated in vacuo twice. The solid was then suspended in ethyl acetate with vigorous stirring and filtered. After repeating this ethyl acetate washing procedure the solid was dried overnight in vacuo to give 46.6 g (42%) of a white solid.

Workup

  1. temperaturethe reaction was heated to reflux
  2. temperatureat reflux for an additional 48 h
  3. customThe solvent was then removed in vacuo
  4. concentrationconcentrated in vacuo twice
  5. stirringwith vigorous stirring
  6. filtrationfiltered
  7. customwas dried overnight in vacuo

Sources & evidence

ORD record
ord-d92e905386224161a9f1d33d433d2443
Source dataset
uspto-grants-1998_01
Patent number
US05710130

Reaction notes

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