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

HRID 426235Notes

Reaction equation

HRID 426235 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N: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(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:1]2[C:12](=[O:13])[C:11]3[C:10](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:9]2=[O:14])[CH:7]=1

Participants

5

Reactant 3

HCID 15332-Amino-4-methylpyridineHCID 6811Phthalic AnhydrideHCID 8471Triethylamine

Product 1

HCID 109990494-Methyl-2-phthalimidopyridineYield 56%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 2-Amino-4-methylpyridine (21.6 g, 0.2 mol) and phthalic anhydride (29.6 g, 0.2 mol) in toluene (160 ml), was added triethylamine (2.8 ml, 0.02 mol). The mixture was refluxed for 5 hr. After cooling to room temperature, the mixture was evaporated in vacuo and the residue was suspended in acetic anhydride (250 ml). The mixture was then heated to reflux for 4 hr until the solid dissolves completely. After cooling to room temperature, white precipitate was collected by filtration and washed with acetic anhydride and hexane, and dried in high vacuo to give 26.6 g (56%) of 2-(4-methyl-pyridin-2-yl)-isoindole-1,3-dione as a white solid. 1H NMR (200 MHz, CDCl3) δ 2.45 (3H, s), 7.18 (1H, d, J=5.0 Hz), 7.25 (1H, s), 7.76-7.99 (4H, m), 8.53 (1H, d, J=5.0 Hz). m/z (EI) 238 (M+).

Workup

  1. temperatureThe mixture was refluxed for 5 hr
  2. customthe mixture was evaporated in vacuo
  3. temperatureThe mixture was then heated
  4. temperatureto reflux for 4 hr until the solid
  5. dissolutiondissolves completely
  6. temperatureAfter cooling to room temperature
  7. filtrationwhite precipitate was collected by filtration
  8. washwashed with acetic anhydride and hexane
  9. customdried in high vacuo

Sources & evidence

ORD record
ord-95b7b16779884ef08626ad256587b4cf
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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