Formic Acid → 2,6-Bis[1-(4-allyl-2,6-diisopropylphenylimino)ethyl]pyridine

HRID 2250976Notes

Reaction equation

HRID 2250976 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].[CH2:13]([C:16]1[CH:22]=[C:21]([CH:23]([CH3:25])[CH3:24])[C:19]([NH2:20])=[C:18]([CH:26]([CH3:28])[CH3:27])[CH:17]=1)[CH:14]=[CH2:15].C(O)=O>CO>[CH2:13]([C:16]1[CH:17]=[C:18]([CH:26]([CH3:28])[CH3:27])[C:19]([N:20]=[C:1]([C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=[N:20][C:19]3[C:21]([CH:23]([CH3:24])[CH3:25])=[CH:22][C:16]([CH2:13][CH:14]=[CH2:15])=[CH:17][C:18]=3[CH:26]([CH3:28])[CH3:27])[CH3:11])[N:5]=2)[CH3:2])=[C:21]([CH:23]([CH3:24])[CH3:25])[CH:22]=1)[CH:14]=[CH2:15]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 707902,6-DiacetylpyridineHCID 219306712,6-Di(propan-2-yl)-4-(prop-2-en-1-yl)aniline

Product 1

HCID 865938702,6-Bis[1-(4-allyl-2,6-diisopropylphenylimino)ethyl]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution containing 2,6-diacetylpyridine (0.30 g, 1.84 mmol), 4-allyl-2,6-diisopropylaniline (0.80 g, 3.68 mmol), and formic acid (2 ml) in 30 ml dry methanol was refluxed under argon for 14 hours. Yellow solid was collected by filtration and washed with cold methanol (3×5 ml). Recrystallization from CH2Cl2:hexane (1:4) yielded 0.70 g (68%) of yellow, 2,6-bis[1-(4-allyl-2,6-diisopropylphenylimino)ethyl]pyridine crystals. IR (KBr): v(C═N) 1639 cm−1. 1H-NMR (CDCl3): 8.47(d, 2H, Py-Hm), 7.92(t, 1H, Py-Hp), 6.98(s, 4H, Ph-Hm), 6.04(m, 2H, CH═C), 5.12(m, 4H, C═CH2), 3.40(d, 4H, CH2—C═C), 2.75(m, 4H, CH(Me)2), 2.27(s, 6H, CH3), 1.15(d, 24H, C(CH3)2); 13C-NMR(CDCl3): 167.04(C═N), 155.15(Py-C), 144.57(Ph-C), 138.12(Ph-C), 136.79(Py-C), 135.69(Ph-C), 134.75(—CH═), 123.16(Py-C), 122.12(Ph-C), 115.34(═CH2), 40.25(—CH2—), 28.31(C(Me)2), 23.24(CH3), 22.92(CH3), 17.14(CH3). C39H51N3 (561.86 g·mol-1): Anal. Calcd: C, 83.37; H, 9.15; N, 7.48. Found: C, 83.03; H, 9.13; N, 7.55.

Workup

  1. temperaturewas refluxed under argon for 14 hours
  2. filtrationYellow solid was collected by filtration
  3. washwashed with cold methanol (3×5 ml)
  4. customRecrystallization from CH2Cl2:hexane (1:4)

Sources & evidence

ORD record
ord-8ab7c9e5c76a4497952039a3f3276ff2
Source dataset
uspto-grants-2008_01
Patent number
US07319083B2

Reaction notes

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