Methanol → 2,4,6-Trimethyl-N-{[6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridin-2-yl]methyl}aniline

HRID 1944824Notes

Reaction equation

HRID 1944824 reaction equation
[C:1]1([CH3:36])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[N:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][C:18]=2[CH2:27][NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])[N:12]=1.CO.[BH3-]C#N.[Na+]>C(O)=O.O>[CH3:36][C:1]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][C:18]=2[CH2:27][NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])[N:12]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 66795918Mesityl{[6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridin-2-yl]methylene}amine

Product 1

HCID 683933262,4,6-Trimethyl-N-{[6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridin-2-yl]methyl}aniline

Reagents, catalysts & solvents 2

HCID 284Formic AcidCatalystHCID 962WaterSolvent

Procedure

To a solution of 1.25 g (2.67 mmol) of mesityl{[6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridin-2-yl]methylene}amine in 20 ml of methanol 0.27 g (4.30 mmol) of NaBH3CN was added in one portion followed by addition of three drops of 88% formic acid. The reaction mixture was refluxed for 1 h and then poured into 50 ml of water. The crude product was extracted with 2×20 ml of ether. The organic extract was washed by 2×30 ml of water, dried over K2CO3, and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: hexanes-ethyl acetate=5:1, vol.). Yield 1.00 g (80%) of yellow oil. Anal. calc. for C33H33N3: C, 84.04; H, 7.05; N, 8.91. Found: C, 84.19; H, 7.20; N, 8.76. 1H NMR (CDCl3): 7.90 (d, J=8.5 Hz, 1H, 4-H in naphthyl), 7.88 (m, 1H, 8-H in naphthyl), 7.74 (m, 1H, 4-H in Py), 7.66 (d, J=8.5 Hz, 1H, 3-H in naphthyl), 7.47 (m, 1H, 7-H in naphthyl), 7.38 (m, 2H, 5,6-H in naphthyl), 7.32 (m, 1H, 3-H in Py), 7.31 (m, 1H, 5-H in Py), 7.02 (m, 1H, 5-H in ortho-tolyl), 7.01 (m, 1H, 3-H in ortho-tolyl), 6.78 (s, 2H, 3,5-H in mesityl), 6.62 (m, 1H, 4-H in ortho-tolyl), 6.51 (m, 1H, 6-H in ortho-tolyl), 4.31 (m, 2H, PyCH2N), 4.22 (m, 2H, NaphCH2N), 3.94 (br. s, 2H, NH), 2.21 (s, 3H, Me in ortho-tolyl), 2.19 (s, 6H, 2,6-Me in mesityl), 2.10 (s, 3H, 4-Me in mesityl).

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. extractionThe crude product was extracted with 2×20 ml of ether
  3. extractionThe organic extract
  4. washwas washed by 2×30 ml of water
  5. dry with materialdried over K2CO3
  6. customevaporated to dryness
  7. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: hexanes-ethyl acetate=5:1, vol.)

Sources & evidence

ORD record
ord-e1d17cf6e6f74214a7bb14ed0898d8e1
Source dataset
uspto-grants-2013_03
Patent number
US08394902B2

Reaction notes

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