2,6-Dimethylaniline → 29167-92-8

HRID 1296733Notes

Reaction equation

HRID 1296733 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[CH3:9][C:10]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:11]=1[NH2:12]>C(O)=O.CO>[CH3:9][C:10]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:11]=1[N:12]=[CH:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

5

Reactant 2

HCID 68962,6-DimethylanilineHCID 142732-Pyridinecarboxaldehyde

Product 1

HCID 85016329167-92-8

Reagents, catalysts & solvents 2

HCID 284Formic AcidCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-pyridine-carboxaldehyde (10 ml, 0.1 mole), 2,6-dimethylaniline (12.9 ml, 0.1 mole), 3 drops of formic acid and 30 ml methanol was stirred for five hours. The methanol was removed under vacuum. An oil-like residue was recrystallized from n-hexane. 2-(N-(2,6-dimethylphenyl)-iminomethyl)-pyridine was isolated as yellow crystals. Yield: 13.6 g (62%). 1H NMR (200 MHz; CDCl3; δ, ppm; J, Hz): 2.17 s (6H, CH3), 6.94-7.12 m (3H, C6H3), 7.39 d,d,d (1H, H(5) 3J4,5=7.5, 3J5,6=4.9, 4J3,5=1.3); 7.83 t,d,d (1H, H(4) 3J=7.7, 4J4,6=1.8, 5J=0.6); 8.28 d,t (1H, H(3) 3J3,4=7.9, J=1.1); 8.35 s (1H, HC═N); 8.71 d,d,d (1H, H(6) 3J5,6=4.9, 4J4,6=1.6, 5J3,6=1.0). 13C NMR, DEPT (50 MHz; CDCl3; δ, ppm): 18.3 (CH3), 121.2 (C(3)H), 124.0 (C(4′)H), 125.3 (C(5)H), 126.8 (C(2′,6′)), 128.1 (C(3′,5′)H), 136.7 (C(4)H), 149.6 (C(6)H), 150.3 (C(1′)), 154.4 (C(2)), 163.4 (HC═N).

Workup

  1. customThe methanol was removed under vacuum
  2. customAn oil-like residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-ca8edf3ecd7c4ce498575ac9d5cfecc4
Source dataset
uspto-grants-2007_07
Patent number
US07247687B2

Reaction notes

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