O-Toluidine → 2,6-Bis[1-(2-methylphenylimino)ethyl]pyridine

HRID 2297071Notes

Reaction equation

HRID 2297071 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH3:11])[N:5]=1)(=O)[CH3:2].[NH2:13][C:14]1[C:15]([CH3:20])=[CH:16][CH:17]=[CH:18][CH:19]=1>C(O)=O.C(Cl)Cl>[CH3:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[N:13]=[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=[N:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[CH3:11])[N:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 7242O-ToluidineHCID 707902,6-Diacetylpyridine

Product 1

HCID 112719622,6-Bis[1-(2-methylphenylimino)ethyl]pyridineYield 45.9%

Reagents, catalysts & solvents 2

HCID 284Formic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

One g of 2,6-diacetylpyridine and 3.0 ml of o-toluidine were added to an Erlenmeyer flask with 20 ml of methylene chloride. A stirbar and 5 drops of 97% formic acid were added, and the flask was sealed and the solution was stirred for 40 hours. The solvent was then removed in vacuo, and the flask was placed in the freezer at −30° C. The resulting viscous oil was washed with cold methanol, and a yellow solid formed and was isolated by filtration and identified by 1H NMR as the desired product (959 mg, 45.9%). 1H NMR (CDCl3): δ8.38(d, 2, Hpyr), 7.86(t, 1, Hpyr), 7.20(m, 4, Haryl), 7.00(t, 2, Haryl), 6.67(d, 2, Haryl), 2.32(s, 6, N═C—CH3), 2.10(s, 6, CH3 aryl)

Workup

  1. customthe flask was sealed
  2. customThe solvent was then removed in vacuo
  3. customwas placed in the freezer at −30° C
  4. washThe resulting viscous oil was washed with cold methanol
  5. customa yellow solid formed
  6. customwas isolated by filtration

Sources & evidence

ORD record
ord-ff883580a14d4cc692da1d28d560db19
Source dataset
uspto-grants-2002_12
Patent number
US06489497B1

Reaction notes

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