2,4,6-Trimethylaniline → Mesityl{[6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridin-2-yl]methylene}amine

HRID 1944823Notes

Reaction equation

HRID 1944823 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1[C:20]1[N:25]=[C:24]([CH:26]=O)[CH:23]=[CH:22][CH:21]=1.[CH3:28][C:29]1[CH:35]=[C:34]([CH3:36])[CH:33]=[C:32]([CH3:37])[C:30]=1[NH2:31]>C(O)C>[C:29]1([CH3:28])[CH:35]=[C:34]([CH3:36])[CH:33]=[C:32]([CH3:37])[C:30]=1[N:31]=[CH:26][C:24]1[CH:23]=[CH:22][CH:21]=[C:20]([C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:18]=[CH:19][C:10]=2[CH2:9][NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[N:25]=1

Participants

4

Reactant 2

HCID 69132,4,6-TrimethylanilineHCID 866633926-(2-{[(2-Methylphenyl)amino]methyl}-1-naphthyl)pyridine-2-carbaldehyde

Product 1

HCID 66795918Mesityl{[6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridin-2-yl]methylene}amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.50 g (4.26 mmol) of 6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridine-2-carbaldehyde and 0.58 g (4.26 mmol) 2,4,6-trimethylaniline in 15 ml of dry ethanol was refluxed for 3 h. The resulting mixture was evaporated to dryness. The product was isolated from the residue by flash chromatography on silica gel 60 (40-63 um; eluent: hexanes-ethyl acetate=5:1, vol.). Yield 1.80 g (90%) of yellow oil. Anal. calc. for C33H31N3: C, 84.40; H, 6.65; N, 8.95. Found: C, 84.62; H, 6.73; N, 8.88. 1H NMR (CDCl3): 8.37 (m, 1H, 3-H in Py), 8.36 (s, 1H, CH═N), 7.97 (m, 1H, 4-H in Py), 7.93 (d, J=8.3 Hz, 1H, 4-H in naphthyl), 7.90 (m, 1H, 8-H in naphthyl), 7.68 (d, J=8.3 Hz, 1H, 3-H in naphthyl), 7.66 (m, 1H, 5-H in Py), 7.49 (m, 1H, 7-H in naphthyl), 7.39-7.44 (5,6-H in naphthyl), 7.03 (m, 1H, 5-H in Ph), 7.01 (m, 1H, 3-H in ortho-tolyl), 6.89 (s, 2H, 3,5-H in mesityl), 6.62 (m, 1H, 4-H in ortho-tolyl), 6.65 (m, 1H, 6-H in ortho-tolyl), 4.27 (m, 2H, CH2N), 3.97 (br. s, 1H, NH), 2.29 (s, 3H, Me in ortho-tolyl), 2.14 (s, 6H, 2,6-Me in mesityl), 2.08 (s, 3H, 4-Me in mesityl).

Workup

  1. temperaturewas refluxed for 3 h
  2. customThe resulting mixture was evaporated to dryness
  3. customThe product was isolated from the residue by flash chromatography on silica gel 60 (40-63 um; eluent: hexanes-ethyl acetate=5:1, vol.)

Sources & evidence

ORD record
ord-c31fc477d4074d8e9d60d451f6cb8e34
Source dataset
uspto-grants-2013_03
Patent number
US08394902B2

Reaction notes

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