1-Naphthylamine → HCID 22171932, compound

HRID 1293498Notes

Reaction equation

HRID 1293498 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH3:11])[N:5]=1)(=[O:3])[CH3:2].[NH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[C:14]1([N:13]=[C:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([C:1](=[O:3])[CH3:2])[N:5]=2)[CH3:11])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 86401-NaphthylamineHCID 707902,6-Diacetylpyridine

Product 1

HCID 22171932HCID 22171932, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,6-Diacetylpyridine (5.49 g, 33.6 mmol) and 1-aminonaphthalene (4.8 g, 33.5 mmol) were dissolved in 100 ml of toluene. To this solution molecular sieves (4 Å) were added. After standing for 20 hours at room temperature, the mixture was filtered. The solvent was removed in vacuo. The resulting mixture of 2,6-diacetylpyridine, 2,6-bis-[1-(1-naphthylimino)ethyl] pyridine and 2-[1-(1-naphthylimino)ethyl]-6-acetylpyridine was dissolved in 50 ml THF. The diiminepyridine by-product 2,6-bis-[1-(1-naphthylimino)ethyl]pyridine was removed by selective complexation to a metal halide. FeCl2 (0.79 g , 6.23 mmol) was added in an inert atmosphere. After stirring for 16 hours at room temperature, the solvent was removed in vacuo. Toluene (100 ml) was added to the resulting mixture. The precipitated complex was filtered off over a small layer of silica, yielding a yellow solution. The solvent was removed vacuo. Crystallisation from ethanol yielded 3.25 g of 2-[1-(1-naphthylimino)ethyl]-6-acetylpyridine (6) (33.6%). 1H-NMR (CDCl3) δ 8.65 (d, 1H, Py-Hm), 8.15 (d, 1H, Py-Hm), 7.95 (t, 1H, Py-Hp), 7.87 (d, 1H, ArH), 7.76 (d, 1H, ArH), 7.64 (d, 1H, ArH), 7.4-7.6 (m, 3H, ArH), 6.82 (d, 1H, ArH), 2.79 (s, 3H, Me), 2.38 (s, 3H, Me).

Workup

  1. additionTo this solution molecular sieves (4 Å) were added
  2. filtrationthe mixture was filtered
  3. customThe solvent was removed in vacuo
  4. additionThe resulting mixture of 2,6-diacetylpyridine, 2,6-bis-[1-(1-naphthylimino)ethyl] pyridine and 2-[1-(1-naphthylimino)ethyl]-6-acetylpyridine
  5. dissolutionwas dissolved in 50 ml THF
  6. customThe diiminepyridine by-product 2,6-bis-[1-(1-naphthylimino)ethyl]pyridine was removed by selective complexation to a metal halide
  7. customthe solvent was removed in vacuo
  8. additionToluene (100 ml) was added to the resulting mixture
  9. filtrationThe precipitated complex was filtered off over a small layer of silica
  10. customyielding a yellow solution
  11. customThe solvent was removed vacuo
  12. customCrystallisation from ethanol

Sources & evidence

ORD record
ord-146e9a68001a459cb8c34fcd7821f943
Source dataset
uspto-grants-2007_07
Patent number
US07238764B2

Reaction notes

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