2-Pyridinecarboxaldehyde → 2-(N-(2-iso-propyl-6-methylphenyl)-iminomethyl)-pyridine

HRID 1296734Notes

Reaction equation

HRID 1296734 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[CH:9]([C:12]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:13]=1[NH2:14])([CH3:11])[CH3:10]>C(O)=O.CO>[CH:9]([C:12]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:13]=1[N:14]=[CH:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 142732-PyridinecarboxaldehydeHCID 789206-Isopropyl-o-toluidine

Product 1

HCID 179706922-(N-(2-iso-propyl-6-methylphenyl)-iminomethyl)-pyridine

Reagents, catalysts & solvents 2

HCID 284Formic AcidCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-pyridine-carboxaldehyde (8.5 ml, 0.052 mole), 2-iso-propyl-6-methylaniline (5 ml, 0.052 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-iso-propyl-6-methylphenyl)-iminomethyl)-pyridine was isolated as yellow crystals. Yield: 10.25 g (82.8%). 1H NMR (200 MHz; CDCl3; δ, ppm; J, Hz): 1.18 d (6H, CH(CH3)2, J=6.9), 2.15 s (3H, CH3), 3.03 sept. (1H, CHMe2, J=6.9), 701-7.21 m (3H, C6H3), 7.41 d,d,d (1H, H(5) 3J4,5=7.5, 3J5,6=4.9, 4J3,5=1.3); 7.85 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); 8.33 s (1H, HC═N); 8.73 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): 18.6 (CH3), 23.3 (CH(CH3)2), 27.9 (CHMe2), 121.3 (C(3)H), 123.2 and 124.3 (C(3′)H and C(5′)H), 125.4 (C(5)H), 126.1 (C(6′)Me), 128.0 (C(4′)H), 136.7 (C(4)H), 137.9 (C(2′)i-Pr), 149.3 (C(1′)), 149.7 (C(6)H), 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-b12a8bd430b74a50ab7ba039d4714af2
Source dataset
uspto-grants-2007_07
Patent number
US07247687B2

Reaction notes

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