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

HRID 1944826Notes

Reaction equation

HRID 1944826 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.[CH:28]([C:31]1[CH:37]=[CH:36][CH:35]=[C:34]([CH:38]([CH3:40])[CH3:39])[C:32]=1[NH2:33])([CH3:30])[CH3:29]>C(O)C>[CH:38]([C:34]1[CH:35]=[CH:36][CH:37]=[C:31]([CH:28]([CH3:30])[CH3:29])[C:32]=1[N:33]=[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)([CH3:40])[CH3:39]

Participants

4

Reactant 2

HCID 32484DiisopropylanilineHCID 866633926-(2-{[(2-Methylphenyl)amino]methyl}-1-naphthyl)pyridine-2-carbaldehyde

Product 1

HCID 66799583(2,6-Diisopropylphenyl){[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 0.75 g (4.26 mmol) of 2,6-diisopropylaniline in 15 ml of dry ethanol was refluxed for 3 h. Crystals precipitated from this mixture at 0° C. were collected, washed by 3×5 ml of cold ethanol, and dried in vacuum. Yield 1.92 g (88%) of yellowish crystalline solid. Anal. calc. for C36H37N3: C, 84.50; H, 7.29; N, 8.21. Found: C, 84.73; H, 7.41; N, 8.02. 1H NMR (CDCl3): 8.35 (m, 1H, 8-H in naphthyl), 8.33 (s, 1H, CH═N), 7.98 (m, 1H, 4-H in Py), 7.92 (d, J=8.6 Hz, 1H, 4-H in naphthyl), 7.89 (m, 1H, 5-H in naphthyl), 7.68 (d, J=8.6 Hz, 1H, 3-H in naphthyl), 7.57 (m, 1H, 3-H in Py), 7.40-7.50 (m, 3H, 5-H in Py and 6,7-H in naphthyl), 6.98-7.17 (m, 5H, 3,4,6-H in 2,6-disopropylphenyl and 3,5-H in ortho-tolyl), 6.61 (m, 1H, 4-H in ortho-tolyl), 6.53 (m, 1H, 6-H in ortho-tolyl), 4.29 (m, 2H, CH2N), 3.93 (br. s, 1H, NH), 2.96 (sept, J=6.8 Hz, 2H, CHMe2), 2.06 (s, 3H, Me in ortho-tolyl), 1.16 (d, J=6.8 Hz, 6H, CHMeMe′), 1.15 (d, J=6.8 Hz, 6H, CHMeMe').

Workup

  1. temperaturewas refluxed for 3 h
  2. customCrystals precipitated from this mixture at 0° C.
  3. customwere collected
  4. washwashed by 3×5 ml of cold ethanol
  5. customdried in vacuum

Sources & evidence

ORD record
ord-87b25c1a86d74316946e9d4d8d4fea77
Source dataset
uspto-grants-2013_03
Patent number
US08394902B2

Reaction notes

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